supporting - royal society of chemistry · s1 supporting information exploration of the active site...
TRANSCRIPT
S1
Supporting Information
Exploration of the active site of β4GalT7: Modifications of the
aglycon of aromatic xylosides Anna Siegbahn,a# Karin Thorsheim,a# Jonas Ståhle,b Sophie Manner,a Christoffer Hamark,b
Andrea Persson,c Emil Tykesson,c Katrin Mani,c Gunilla Westergren-Thorsson,c Göran
Widmalm,b Ulf Ellervika*
a Center for Analysis and Synthesis, Center for Chemistry and Chemical Engineering, Lund University, P.O.
Box 124, SE-221 00 Lund, Sweden b Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm,
Sweden c Department of Experimental Medical Science, Lund University, BMC, SE-221 00 Lund, Sweden # These authors contributed equally to this work
Table of Contents Mass analysis ............................................................................................................................ 3
Cloning, expression and purification of β4GALT7 .............................................................. 4 1H-NMR Phenyl β-D-xylopyranoside (3) ................................................................................. 5 13C-NMR Phenyl β-D-xylopyranoside (3) ................................................................................ 6 1H-NMR 1-Naphthyl β-D-xylopyranoside (4) .......................................................................... 7 13C-NMR 1-Naphthyl β-D-xylopyranoside (4) ......................................................................... 8 1H-NMR 4-Phenylphenyl β-D-xylopyranoside (5) ................................................................... 9 13C-NMR 4-Phenylphenyl β-D-xylopyranoside (5) ................................................................ 10 1H-NMR (9-Anthracene)-methyl β-D-xylopyranoside (6) ...................................................... 11 13C-NMR (9-Anthracene)-methyl β-D-xylopyranoside (6) ..................................................... 12 1H-NMR 2-Naphthyl 1-thio-β-D-xylopyranoside (7) ............................................................. 13 13C-NMR 2-Naphthyl 1-thio-β-D-xylopyranoside (7) ............................................................ 14 1H-NMR 2-Naphthyl β-D-xylopyranosyl sulfone (8) ............................................................. 15 13C-NMR 2-Naphthyl β-D-xylopyranosyl sulfone (8) ............................................................ 16 1H-NMR 2-Naphthyl β-L-xylopyranoside (10) ....................................................................... 17 13C-NMR 2-Naphthyl β-L-xylopyranoside (10) ...................................................................... 18 1H-NMR 2-Naphthyl α-D-xylopyranoside (11) ...................................................................... 19
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2015
S2
13C-NMR 2-Naphthyl α-D-xylopyranoside (11) ..................................................................... 20 1H-NMR 2-(6-Cyano-naphthyl) β-D-xylopyranoside (19) ..................................................... 21 13C-NMR 2-(6-Cyano-naphthyl) β-D-xylopyranoside (19) .................................................... 22 1H-NMR 2-Naphthyl 1-thio-α-L-arabinopyranoside (23) ....................................................... 23 13C-NMR 2-Naphthyl 1-thio-α-L-arabinopyranoside (23) ...................................................... 24 1H-NMR α-L-Arabinopyranoside 2-naphthyl sulfone (24) ..................................................... 25 13C-NMR α-L-Arabinopyranoside 2-naphthyl sulfone (24) ................................................... 26 1H-NMR (2-Naphthyl)-methyl α-L-arabinopyranoside (25) .................................................. 27 13C-NMR (2-Naphthyl)-methyl α-L-arabinopyranoside (25) ................................................. 28 1H-NMR 5-(2-Naphthoxy)-3-oxo-1-pentyl α-L-arabinopyranoside (26) ............................... 29 13C-NMR 5-(2-Naphthoxy)-3-oxo-1-pentyl α-L-arabinopyranoside (26) .............................. 30 1H-NMR 1-Naphthyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (29) ......................................... 31 13C-NMR 1-Naphthyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (29) ........................................ 32 1H-NMR 4-Phenylphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (30) .................................. 33 13C-NMR 4-Phenylphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (30) ................................. 34 1H-NMR 2-(6-Cyano-naphthyl) 2,3,4-tri-O-acetyl-β-D-xylopyranoside (31) ........................ 35 13C-NMR 2-(6-Cyano-naphthyl) 2,3,4-tri-O-acetyl-β-D-xylopyranoside (31) ....................... 36 1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (32) .............................. 37 13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (32) ............................. 38 1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl β-D-xylopyranosyl sulfone (33) .............................. 39 13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl β-D-xylopyranosyl sulfone (33) ............................. 40 1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl β-L-xylopyranoside (35) .......................................... 41 13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl β-L-xylopyranoside (35) ......................................... 42 1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl 1-thio-α-L-arabinopyranoside (38) .......................... 43 13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl 1-thio-α-L-arabinopyranoside (38) ......................... 44 1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl α-L-arabinopyranosyl sulfone (39) .......................... 45 13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl α-L-arabinopyranosyl sulfone (39) ........................ 46 1H-NMR (2-Naphthyl)-methyl 2,3,4-tri-O-acetyl α-L-arabinopyranoside (40) ..................... 47 13C-NMR (2-Naphthyl)-methyl 2,3,4-tri-O-acetyl α-L-arabinopyranoside (40) .................... 48 1H-NMR 5-Chloro-3-oxo-1-pentyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside (42) ............... 49 13C-NMR 5-Chloro-3-oxo-1-pentyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside (42) .............. 50 1H-NMR 5-(2-Naphthoxy)-3-oxo-1-pentyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside (43) .. 51 13C-NMR 5-(2-Naphthoxy)-3-oxo-1-pentyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside (43) . 52
S3
Mass analysis Table S1. HRMS for all galactosylated products.
a HRMS for [M+NH4]+
Acceptor substrate
Galactosylation product Chemical formula
HRMS calcd for [M+H]+
HRMS found
1 C21H26O10 439.1599 439.1598 2 C12H22O10 327.1286 327.1287 3 C17H24O10 389.1442 389.1441 4 C21H26O10 439.1599 439.1598 5 C23H28O10 465.1755 465.1755 6 C26H30O10 520.2177a 520.2179 7 C21H26O9S 455.1370 455.1370 8 C21H26O11S 487.1269 487.1270 9 C22H28O9 437.1806 437.1804 12 C22H28O10 453.1755 453.1755 13 C23H30O11 483.1861 483.1858 14 C25H34O12 527.2123 527.2123 15 C27H38O13 571.2385 571.2388 16 C22H28O11 486.1973a 486.1972 17 C21H26O11 455.1548 455.1549 18 C23H28O12 497.1654 497.1655 19 C22H25NO10 464.1551 464.1550
S4
Cloning, expression and purification of β4GALT7 The part of the b4GALT7 open reading frame (sequence harmonized for expression in E.
Coli, Genewiz) corresponding to aa 82 to aa 327 was subcloned into the NcoI and NotI sites
of a pET-41a(+) (Merck Millipore) expression vector using the following primers (Sigma):
Forward (NcoI restriction site in bold letters)
aa 82: 5’-GCATCTCCCATGGAGCATTGGGAGGAAGATGCCAGTT-3'
Reverse (NotI restriction site in bold letters) aa 327: 5’-
GCATCTGCGGCCGCATTAGCTAAATGTACACCAAGGGGTTGC-3’
The plasmid product, pET-41a(+)-β4GALT7aa82, was amplified (Library Efficiency DH5α
bacteria, Invitrogen), purified (HiSpeed Plasmid Midi Kit, Qiagen) and sequenced (Eurofins
MWG Operon). BL21(DE3) E. Coli bacteria (Merck Millipore) were transformed with pET-
41a(+)-β4GALT7aa82 and grown on LB agar containing kanamycin (30 mg/ml). A resistant
colony was transferred to selective LB medium and grown at 37 °C with shaking at 250 rpm
to OD600≈0.5. Expression was induced at 32 °C with IPTG (0.56 mM, Sigma) and culture
was left shaking at 250 rpm over night. Cells were pelleted and then lysed with Cellytic (1X,
Sigma) in Tris (20 mM, pH 7.6), NaCl (500 mM), Benzonase (50 U/ml, Sigma), lysozyme
(0.2 mg/ml, Sigma) and PMSF (1 mM) for 20 min at 22 °C. Clarified lysate was applied to an
equilibrated HisTrap HP column (GE Healthcare) at a flowrate of 1 ml/min. The column was
washed with a phosphate buffer (20 mM, pH 7.4) containing NaCl (500 mM) and imidazole
(40 mM), after which the protein was eluted by an imidazole gradient (40-250 mM). Protein
purity for each eluted fraction was analyzed by SDS-PAGE on a Bis-Tris 4-12 % gel in
MOPS buffer (Invitrogen), visualized by Brilliant Blue G colloidal (Sigma). Fractions
containing pure protein were pooled and buffer exchanged into TBS (20 mM, pH 7.9) on PD-
10 columns (GE Healthcare).
S5
1H-NMR Phenyl β-D-xylopyranoside (3)
23
45
67
89
10
ppm3.353
3.3793.4023.4233.4303.4383.4443.4473.4503.4703.5483.5563.5613.5703.5733.5763.5833.5873.5953.6023.6093.8943.9073.9223.9364.8504.8564.8624.8696.9826.9846.9877.0017.0037.0057.0197.0217.0247.0307.0377.0397.0427.0447.0537.0587.0617.0647.0667.2497.2557.2607.2687.2737.2777.2837.2907.2937.2957.301
1.081.980.99
1.00
1.09
1.001.941.96
TD0 1
D1 0.00100000 sec
TE 293.4 K
DE 6.50 usec
DW 69.333 usec
RG 71.8
AQ 3.9998901 sec
FIDRES 0.125005 Hz
SWH 7211.539 Hz
DS 2
NS 32
SOLVENT MeOD
TD 57690
PULPROG zg30
PROBHD 5 mm PABBO BB−
INSTRUM spect
Time 15.30
Date_ 20141209
PROCNO 1
EXPNO 1
NAME KT−D150
OHO H
OOHO
3
S6
13C-NMR Phenyl β-D-xylopyranoside (3)
2030
4050
6070
8090
100
110
120
130
140
150
160
170
180
190
200
210
ppm
66.85970.99074.71177.679
102.815
117.750
123.445
130.393
158.894
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
6322
MH
zSI
3
2768
P1
9.8
0 us
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100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
93.8
KD
E
6.5
0 us
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W
20.8
00 u
sec
RG
5
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Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
8
000
SOLV
ENT
M
eOD
TD
480
74PU
LPRO
G
zgd
c30
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5
mm
PA
BBO
BB−
INST
RUM
s
pect
Tim
e
2
2.27
Dat
e_
201
4120
9PR
OCN
O
1EX
PNO
3
NA
ME
K
T−D
150
OHO H
OOHO
3
S7
1H-NMR 1-Naphthyl β-D-xylopyranoside (4)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
3.3783.4043.4063.4323.4593.4813.5033.6043.6173.6293.6363.6393.6513.6583.6643.9423.9553.9703.983
5.0545.072
7.1287.1477.3627.3827.4027.4427.4557.4607.4707.4797.4857.4977.5027.5147.5357.7997.8087.8167.8228.3488.3558.3628.372
1.1571.0882.098
1.063
1.074
1.049
1.1263.135
1.027
1.000
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0078
MH
zSI
13
1072
P1
9.8
0 us
ecN
UC1
1
HSF
O1
400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
.3 K
DE
6
.50
usec
DW
69
.333
use
cRG
203
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
SWH
7211
.539
Hz
DS
2N
S
32
SOLV
ENT
M
eOD
TD
576
90PU
LPRO
G
zg
30PR
OB
HD
5
mm
PA
BB
O B
B−
INST
RUM
s
pect
Tim
e
1
3.47
Dat
e_
201
4101
4PR
OCN
O
1EX
PNO
2
NA
ME
SM
−D11
5_D
OHO H
OOHO
4
S8
13C-NMR 1-Naphthyl β-D-xylopyranoside (4)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
66.980
71.07174.85777.828
103.276
110.451
123.149123.291126.335126.806127.349127.456128.439136.056
154.471
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
6270
MH
zSI
3
2768
P1
9.8
0 us
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100
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8298
MH
z==
====
== C
HA
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===
====
=
TD0
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11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
94.4
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
4
000
SOLV
ENT
M
eOD
TD
480
74PU
LPRO
G
zgd
c30
PRO
BHD
5
mm
PA
BBO
BB−
INST
RUM
s
pect
Tim
e
0
.40
Dat
e_
201
4101
5PR
OCN
O
1EX
PNO
3
NA
ME
SM
−D11
5_D
OHO H
OOHO
4
S9
1H-NMR 4-Phenylphenyl β-D-xylopyranoside (5)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
3.3563.3823.3853.4103.4323.4443.4493.4533.4623.4843.5773.5813.5913.5943.6163.9153.9283.9433.957
4.8984.916
7.1137.1207.1257.1377.1427.1497.2667.2697.2877.3037.3057.3817.4017.4157.4197.5287.5357.5407.5537.5577.5657.5737.576
3.1961.049
1.043
1.369
2.0731.0002.0794.168
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0079
MH
zSI
13
1072
P1
9.8
0 us
ecN
UC1
1
HSF
O1
400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
.2 K
DE
6
.50
usec
DW
69
.333
use
cRG
181
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
SWH
7211
.539
Hz
DS
2N
S
32
SOLV
ENT
M
eOD
TD
576
90PU
LPRO
G
zg
30PR
OB
HD
5
mm
PA
BB
O B
B−
INST
RUM
s
pect
Tim
e
8
.57
Dat
e_
201
4091
1PR
OCN
O
1EX
PNO
4
NA
ME
SM
−D12
3_D
OHO H
OOHO
5
S10
13C-NMR 4-Phenylphenyl β-D-xylopyranoside (5)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
66.960
71.04974.77477.749
102.889
118.098
127.673127.893128.952129.798
136.792
141.965
158.473
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
6272
MH
zSI
3
2768
P1
9.8
0 us
ecN
UC1
1
3CSF
O1
100
.622
8298
MH
z==
====
== C
HA
NN
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===
====
=
TD0
1D
11
0.0
3000
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D1
0
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0000
0 se
cTE
2
94.6
KD
E
6.5
0 us
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W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
1
500
SOLV
ENT
M
eOD
TD
480
74PU
LPRO
G
zgd
c30
PRO
BHD
5
mm
PA
BBO
BB−
INST
RUM
s
pect
Tim
e
7
.32
Dat
e_
201
4091
2PR
OCN
O
1EX
PNO
6
NA
ME
SM
−D12
3_D
OHO H
OOHO
5
S11
1H-NMR (9-Anthracene)-methyl β-D-xylopyranoside (6)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm3.181
3.2003.2043.2183.2233.2443.2463.2503.2723.2943.4853.5143.5273.5353.5393.5493.5533.5613.5743.5953.6493.9914.0054.0204.0334.4424.461
5.6515.6795.8195.847
7.4647.4667.4807.4827.4877.5017.5037.5367.5407.5527.5587.5627.5757.5788.0358.0568.4808.5028.530
3.354
1.274
0.988
0.941
1.0161.000
1.9602.146
2.015
2.985
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0078
MH
zSI
13
1072
P1
9.8
0 us
ecN
UC1
1
HSF
O1
400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
295
.1 K
DE
6
.50
usec
DW
69
.333
use
cRG
181
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
SWH
7211
.539
Hz
DS
2N
S
128
SOLV
ENT
M
eOD
TD
576
90PU
LPRO
G
zg
30PR
OB
HD
5
mm
PA
BB
O B
B−
INST
RUM
s
pect
Tim
e
1
6.51
Dat
e_
201
4091
5PR
OCN
O
1EX
PNO
1
NA
ME
SM
−D13
7_C
OHO H
OOHO
6
S12
13C-NMR (9-Anthracene)-methyl β-D-xylopyranoside (6)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
63.77067.184
71.29874.83377.888
103.997
125.607126.099127.323128.985129.635129.948132.588132.904
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
6271
MH
zSI
3
2768
P1
9.8
0 us
ecN
UC1
1
3CSF
O1
100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
94.9
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
5
000
SOLV
ENT
M
eOD
TD
480
74PU
LPRO
G
zgd
c30
PRO
BHD
5
mm
PA
BBO
BB−
INST
RUM
s
pect
Tim
e
2
.30
Dat
e_
201
4091
8PR
OCN
O
1EX
PNO
3
NA
ME
SM
−D13
7_C
OHO H
OOHO
6
S13
1H-NMR 2-Naphthyl 1-thio-β-D-xylopyranoside (7)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
3.2293.2493.2513.2743.3503.3723.3933.4553.4683.4783.4813.4903.4933.5023.5153.9543.9663.9823.9944.6564.679
7.4517.4647.4697.4797.4887.4947.5067.5817.5857.6037.6077.7907.8127.8197.8267.8337.8428.0098.011
1.8201.3371.069
0.999
1.000
1.9531.024
3.062
1.039
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0080
MH
zSI
13
1072
P1
9.8
0 us
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400
.133
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MH
z==
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== C
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===
====
=
TD0
1D
1
0.0
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TE
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.2 K
DE
6
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69
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cRG
161
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3.99
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8
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576
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5
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B−
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s
pect
Tim
e
1
1.13
Dat
e_
201
4082
7PR
OCN
O
1EX
PNO
1
NA
ME
SM
−D12
1_D
OHO H
OOHS
7
S14
13C-NMR 2-Naphthyl 1-thio-β-D-xylopyranoside (7)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
70.46670.90973.758
79.221
90.010
127.321127.598128.500128.690129.332130.514131.848132.234133.956135.050
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
6280
MH
zSI
3
2768
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9.8
0 us
ecN
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100
.622
8298
MH
z==
====
== C
HA
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===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
94.6
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
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0.
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892
sec
FID
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0.5
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0 H
zSW
H
240
38.4
61 H
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4
NS
5
12SO
LVEN
T
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4
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11.
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2
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PRO
CNO
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EXPN
O
2N
AM
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SM−D
121_
D
OHO H
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7
S15
1H-NMR 2-Naphthyl β-D-xylopyranosyl sulfone (8)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
10.0
10.5
ppm
3.1453.1603.1713.1813.1913.1993.3473.3633.3693.3803.3873.3943.4853.6253.6473.6703.8503.8623.8783.8904.4304.453
7.6557.6587.6757.6937.6957.7117.7147.7327.7497.7527.8847.8887.9067.9108.0128.0338.0698.0908.1088.540
1.2042.1310.2010.987
1.072
0.046
1.0000.051
2.0121.0141.0062.036
0.984PC
4
.00
GB
0LB
0
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Hz
SSB
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4
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78 M
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SI
1310
72P1
9
.80
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NU
C1
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1
4
00.1
3320
10 M
Hz
====
====
CH
AN
NEL
f1 =
====
===
TD0
1D
1
0.0
0100
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sec
TE
294
.7 K
DE
6
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69
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203
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576
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5
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B−
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pect
Tim
e
1
2.27
Dat
e_
201
4091
2PR
OCN
O
1EX
PNO
1
NA
ME
K
T−D
090
OHO H
OOHS
OO
8
S16
13C-NMR 2-Naphthyl β-D-xylopyranosyl sulfone (8)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
70.22471.03371.237
79.099
93.748
125.208128.754129.052130.035130.591130.633132.602133.492135.276137.047
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
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0
WD
W
EM
SF
100
.612
6271
MH
zSI
3
2768
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9.8
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1
3CSF
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100
.622
8298
MH
z==
====
== C
HA
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=
TD0
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11
0.0
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D1
0
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0 se
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2
94.8
KD
E
6.5
0 us
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20.8
00 u
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5
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0.
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892
sec
FID
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0.5
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0 H
zSW
H
240
38.4
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zD
S
4
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9
000
SOLV
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M
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480
74PU
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G
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5
mm
PA
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BB−
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Tim
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1
.27
Dat
e_
201
4091
4PR
OCN
O
1EX
PNO
3
NA
ME
K
T−D
090
OHO H
OOHS
OO
8
S17
1H-NMR 2-Naphthyl β-L-xylopyranoside (10)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
3.4263.4413.4523.4553.4643.4803.4853.4873.5033.5073.5263.5793.5923.6003.6043.6143.6173.6263.6393.9543.9673.9823.9955.0195.037
7.2527.2587.2747.2807.3307.3337.3477.3507.3537.3677.3717.4117.4187.4287.4317.4357.4497.4527.7557.7757.798
3.1411.063
1.012
1.000
0.9761.0292.140
3.160
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
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400
.130
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MH
zSI
13
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4
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3340
11 M
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27.
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9.1
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0.0
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300
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6
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69
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576
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Tim
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8
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Dat
e_
201
3081
2PR
OCN
O
1EX
PNO
1
NA
ME
K
H−C
002
OO
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OH
10
S18
13C-NMR 2-Naphthyl β-L-xylopyranoside (10)
2030
4050
6070
8090
100
110
120
130
140
150
160
170
180
190
200
210
ppm
67.00371.07474.81677.751
102.898
111.867
119.994125.267127.398128.125128.614130.356131.303135.833
156.662
SF
100
.612
6271
MH
zSI
3
2768
SFO
2
4
00.1
3160
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Hz
PL12
W
0
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4 W
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27.
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12
1
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−5.
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80.0
0 us
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====
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====
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SFO
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73.
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2
2.50
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e_
201
3081
2PR
OCN
O
1EX
PNO
3
NA
ME
K
H−C
002
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10
S19
1H-NMR 2-Naphthyl α-D-xylopyranoside (11)
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
10.0
10.5
ppm
3.5943.6023.6053.6113.6253.6343.6633.6743.8373.8573.880
5.6155.624
7.2957.3017.3177.3247.3457.3637.3657.4047.4077.4247.4427.4447.4927.4987.7317.7527.7787.7937.801
4.05
0.96
1.00
2.021.041.00
3.04
PC 4.00
GB 0
LB 0.30 Hz
SSB 0
WDW EM
SF 400.1300078 MHz
SI 131072
P1 9.80 usec
NUC1 1H
SFO1 400.1332010 MHz
======== CHANNEL f1 ========
TD0 1
D1 0.00100000 sec
TE 293.6 K
DE 6.50 usec
DW 69.333 usec
RG 128
AQ 3.9998901 sec
FIDRES 0.125005 Hz
SWH 7211.539 Hz
DS 2
NS 8
SOLVENT MeOD
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Time 8.10
Date_ 20141110
PROCNO 1
EXPNO 1
NAME
KT
−alf
aXyl
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11
S20
13C-NMR 2-Naphthyl α-D-xylopyranoside (11)
2030
4050
6070
8090
100
110
120
130
140
150
160
170
180
190
200
210
ppm
63.713
71.39873.40375.160
99.141
111.924
120.106125.222127.381128.087128.612130.399131.198135.860
156.107
PC
1.4
0G
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1.0
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100
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5
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11
S21
1H-NMR 2-(6-Cyano-naphthyl) β-D-xylopyranoside (19)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
3.3023.3063.3103.3143.3183.3493.4583.4663.4813.4913.4943.5013.5053.5073.5193.5243.5463.5883.6003.6223.9613.9743.9894.002
5.0955.113
7.3797.3857.4027.4087.4937.4987.5867.5907.6077.6117.9067.9247.9298.278
3.1211.043
1.033
1.019
0.017
0.018
1.0271.0321.017
2.065
1.000
PC
4.0
0G
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0.3
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400
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13
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201
4090
5PR
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NA
ME
S
MD
127B
OHO H
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CN19
S22
13C-NMR 2-(6-Cyano-naphthyl) β-D-xylopyranoside (19)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
67.03870.96374.66377.638
102.351
108.317111.571
120.303121.847127.882129.560129.917131.273135.007137.618
159.089
PC
1.4
0G
B
0
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1.0
0 H
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0
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W
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100
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MH
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0 se
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2
95.2
KD
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6.5
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20.8
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sec
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5
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0.
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sec
FID
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0.5
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240
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4
NS
5
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905
PRO
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O
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S23
1H-NMR 2-Naphthyl 1-thio-α-L-arabinopyranoside (23)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
3.6003.6083.6163.6203.6283.6473.6513.7293.7503.7703.8963.9003.9043.9093.9133.9183.9994.0084.0304.0394.7564.777
7.4327.4367.4497.4537.4597.4667.4727.4797.4837.4957.5007.5837.5877.6047.6097.7797.8017.8097.8147.8328.0058.008
2.1691.0391.0311.077
1.000
2.1301.120
3.244
1.102
PC
4.0
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B
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0.3
0 H
zSS
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0
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400
.130
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13
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9.8
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294
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6
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69
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3.99
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201
4091
2PR
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23
S24
13C-NMR 2-Naphthyl 1-thio-α-L-arabinopyranoside (23)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
69.51269.56471.64574.958
90.222
127.121127.542128.439128.680129.313129.979130.866133.595133.783135.131
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
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100
.612
6271
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3
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9.8
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100
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8298
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====
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=
TD0
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11
0.0
3000
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20.8
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0.
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FID
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0.5
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4
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9
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480
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Tim
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2
2.43
Dat
e_
201
4091
3PR
OCN
O
1EX
PNO
3
NA
ME
K
T−D
086
OHO
OHS
OH
23
S25
1H-NMR α-L-Arabinopyranoside 2-naphthyl sulfone (24)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
10.0
10.5
ppm
3.4063.4193.4283.4713.5003.6213.6983.7033.7283.7333.7593.7813.7953.8033.8174.4334.4554.6364.6414.9584.9735.2985.313
7.6767.6937.7117.7137.7307.7327.7507.7677.8537.8577.8747.8788.0658.0858.1268.1488.1938.2138.540
1.1021.0561.0251.0411.030
0.9930.896
0.886
0.896
1.0221.0371.0151.0421.0191.012
1.000PC
4
.00
GB
0LB
0
.30
Hz
SSB
0W
DW
EMSF
4
00.1
3000
36 M
Hz
SI
1310
72P1
9
.80
usec
NU
C1
1H
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1
4
00.1
3320
10 M
Hz
====
====
CH
AN
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f1 =
====
===
TD0
1D
1
0.0
0100
000
sec
TE
295
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DE
6
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69
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161
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3.99
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1 se
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32
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576
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5
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Tim
e
1
4.55
Dat
e_
201
4092
3PR
OCN
O
1EX
PNO
2
NA
ME
KT−
D09
6.D
MSO
OHO
OHS
OO
OH
24
S26
13C-NMR α-L-Arabinopyranoside 2-naphthyl sulfone (24)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
66.70867.73270.50273.182
92.597
124.057127.553127.868128.745129.319129.517130.575131.595134.848134.953
PC
1.4
0G
B
0
LB
1.0
0 H
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0
WD
W
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100
.612
8143
MH
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3
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100
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z==
====
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===
====
=
TD0
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11
0.0
3000
000
sec
D1
0
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0000
0 se
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2
94.9
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E
6.5
0 us
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W
20.8
00 u
sec
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5
7A
Q
0.
9999
892
sec
FID
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0.5
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0 H
zSW
H
240
38.4
61 H
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S
4
NS
9
000
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D
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TD
480
74PU
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5
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PA
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INST
RUM
s
pect
Tim
e
8
.00
Dat
e_
201
4092
4PR
OCN
O
1EX
PNO
4
NA
ME
KT−
D09
6.D
MSO
OHO
OHS
OO
OH
24
S27
1H-NMR (2-Naphthyl)-methyl α-L-arabinopyranoside (25)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
3.5153.5243.5383.5463.5503.5543.5813.5853.6403.6573.6623.6793.8153.8193.8233.8273.8313.8353.9043.9123.9353.9434.3424.3594.7774.8074.8895.0085.039
7.4387.4507.4527.4557.4617.4647.4707.4737.4757.4877.5307.5347.5517.5557.8237.8297.8357.8457.8497.881
1.0420.9830.9721.0091.002
1.000
1.091
1.014
1.9630.972
3.0190.954
PC
4.0
0G
B
0
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0.3
0 H
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0
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W
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400
.130
0078
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13
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9.8
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400
.133
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MH
z==
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294
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9
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e_
201
4090
1PR
OCN
O
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1$0(������������.
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25
S28
13C-NMR (2-Naphthyl)-methyl α-L-arabinopyranoside (25)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
66.93869.66171.62372.50774.251
103.911
126.930127.089127.126127.739128.657128.913128.970134.506134.767136.648
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
6271
MH
zSI
3
2768
P1
9.8
0 us
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100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
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D1
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0 se
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2
94.8
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E
6.5
0 us
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20.8
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5
7A
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0.
9999
892
sec
FID
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0.5
0003
0 H
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240
38.4
61 H
zD
S
4
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9
000
SOLV
ENT
M
eOD
TD
480
74PU
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G
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5
mm
PA
BBO
BB−
INST
RUM
s
pect
Tim
e
2
2.59
Dat
e_
201
4090
1PR
OCN
O
1EX
PNO
3
NA
ME
K
T−D
066
OHO
OHO
OH
25
S29
1H-NMR 5-(2-Naphthoxy)-3-oxo-1-pentyl α-L-arabinopyranoside (26)
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
10.0
10.5
ppm3.495
3.5043.5093.5133.5183.5263.5403.5443.5603.5773.5823.5993.7323.7423.7603.7673.7773.7813.7833.7883.7923.7963.8023.8073.8403.8473.8713.8783.9213.9303.9333.9373.9453.9623.9703.9763.9833.9883.9984.2384.2414.2504.2554.2644.8887.1477.1537.1697.1757.2407.2477.2897.2927.3067.3097.3127.3277.3307.3927.3957.4097.4127.4157.4337.7377.7437.7467.758
2.0170.9854.1011.0712.0301.0333.000
0.9730.9780.9630.989
2.948
PC
4.0
0G
B
0
LB
0.3
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0
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W
EM
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400
.130
0078
MH
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13
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400
.133
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MH
z==
====
== C
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===
====
=
TD0
1D
1
0.0
0100
000
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TE
294
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DE
6
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69
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181
AQ
3.99
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32
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M
eOD
TD
576
90PU
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G
zg
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5
mm
PA
BB
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B−
INST
RUM
s
pect
Tim
e
9
.54
Dat
e_
201
4090
1PR
OCN
O
1EX
PNO
1
NA
ME
K
T−D
068
OHO
OH
OH
OO
O
26
S30
13C-NMR 5-(2-Naphthoxy)-3-oxo-1-pentyl α-L-arabinopyranoside (26)
3040
5060
7080
90100
110
120
130
140
150
160
170
180
190
200
210
ppm
66.93468.53269.44069.64170.85071.69372.39874.188
104.986107.733
119.847124.660127.340127.859128.573130.382130.560136.128
158.144
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
6274
MH
zSI
3
2768
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9.8
0 us
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1
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100
.622
8298
MH
z==
====
== C
HA
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EL f1
===
====
=
TD0
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11
0.0
3000
000
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D1
0
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0000
0 se
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2
94.5
KD
E
6.5
0 us
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20.8
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sec
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5
7A
Q
0.
9999
892
sec
FID
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0.5
0003
0 H
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H
240
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4
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9
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M
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TD
480
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5
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PA
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RUM
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pect
Tim
e
2
.32
Dat
e_
201
4090
2PR
OCN
O
1EX
PNO
3
NA
ME
K
T−D
068
OHO
OH
OH
OO
O
26
S31
1H-NMR 1-Naphthyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (29)
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
2.0842.1052.147
3.5793.5983.6093.6284.2634.2744.2934.3055.0425.0535.0605.0725.0795.0915.2885.3075.3255.3595.3755.3935.408
7.0657.0847.3627.3837.4027.4647.4777.4837.4927.5027.5077.5207.5417.5617.8057.8157.8227.8298.1258.1328.1408.149
5.8813.174
1.019
1.012
1.000
1.0202.067
0.983
1.0193.105
0.989
1.007
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
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MH
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13
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400
.133
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MH
z==
====
== C
HA
NN
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===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
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DE
6
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69
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use
cRG
161
AQ
3.99
9890
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S
0
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DS
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S
64
SOLV
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C
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5
7690
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ROG
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D
5 m
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STRU
M
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12.
42D
ate_
2
0140
820
PRO
CNO
1
EXPN
O
1N
AM
E
SM−D
115_
B
OAcOAcO
OAcO
29
S32
13C-NMR 1-Naphthyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (29)
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
200
210
ppm
20.927
20.950
20.960
61.975
68.558
70.126
70.613
98.769
108.892
121.761
122.840
125.778
125.876
125.957
126.721
127.736
134.647
152.497
169.689
169.996
170.046
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
7558
MH
zSI
3
2768
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9.8
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100
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MH
z==
====
== C
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===
====
=
TD0
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11
0.0
3000
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95.2
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E
6.5
0 us
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20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
3
000
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
0.3
1D
ate_
2
0140
821
PRO
CNO
1
EXPN
O
3N
AM
E
SM−D
115_
B
OAcOAcO
OAcO
29
S33
1H-NMR 4-Phenylphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (30)
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
3.5263.5463.5573.5764.2264.2374.2564.2685.0165.0285.0355.0475.0545.0665.2135.2205.2275.2355.2435.2515.2585.2705.2775.2845.2917.0607.0677.0727.0857.0907.0977.3027.3207.3397.4007.4207.4387.5117.5187.5237.5317.5327.5407.5507.553
9.148
1.000
1.000
1.035
3.027
2.034
1.0562.0534.045
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0100
MH
zSI
13
1072
P1
9.8
0 us
ecN
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1
HSF
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400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
.7 K
DE
6
.50
usec
DW
69
.333
use
cRG
36
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
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7211
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Hz
DS
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S
8
SOLV
ENT
C
DCl
3TD
5
7690
PULP
ROG
zg30
PRO
BH
D
5 m
m P
AB
BO
BB
−IN
STRU
M
spe
ctTi
me
8.0
4D
ate_
2
0140
909
PRO
CNO
1
EXPN
O
1N
AM
E
SM−D
123_
C
OAcOAcO
OAcO
30
S34
13C-NMR 4-Phenylphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (30)
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
20.739
20.775
20.795
61.919
68.533
70.197
70.753
98.547
117.137
126.896
127.073
128.318
128.814
136.237
140.470
156.105
169.420
169.861
169.985
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
7688
MH
zSI
3
2768
P1
9.8
0 us
ecN
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1
3CSF
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100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
95.1
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
5
12SO
LVEN
T
CD
Cl3
TD
480
74PU
LPRO
G
zgd
c30
PRO
BHD
5
mm
PA
BBO
BB−
INST
RUM
s
pect
Tim
e
8
.58
Dat
e_
201
4090
9PR
OCN
O
1EX
PNO
2
NA
ME
SM
−D12
3_C
OAcOAcO
OAcO
30
S35
1H-NMR 2-(6-Cyano-naphthyl) 2,3,4-tri-O-acetyl-β-D-xylopyranoside (31)
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
2.0972.1002.112
3.6153.6323.6463.6634.2474.2584.2774.2885.0105.0165.0275.0335.0445.2065.2205.2245.2375.2385.2465.2645.2825.3945.407
7.2607.2627.2687.2847.2917.3717.3777.5587.5627.5797.5837.7807.8027.8137.8368.154
9.363
1.045
1.030
1.071
2.0691.068
1.1661.0371.032
2.082
1.000
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0100
MH
zSI
13
1072
P1
9.8
0 us
ecN
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1
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400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
.6 K
DE
6
.50
usec
DW
69
.333
use
cRG
7
1.8
AQ
3.99
9890
1 se
cFI
DRE
S
0
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005
Hz
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7211
.539
Hz
DS
2N
S
8
SOLV
ENT
C
DCl
3TD
5
7690
PULP
ROG
zg30
PRO
BH
D
5 m
m P
AB
BO
BB
−IN
STRU
M
spe
ctTi
me
15.
05D
ate_
2
0140
903
PRO
CNO
1
EXPN
O
1N
AM
E
SM−D
127_
A
OAcOAcO
OAcO
CN
31
S36
13C-NMR 2-(6-Cyano-naphthyl) 2,3,4-tri-O-acetyl-β-D-xylopyranoside (31)
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
200
210
ppm
20.815
20.858
20.894
61.858
68.298
69.749
70.145
97.875
107.972
110.949
119.379
120.624
127.274
128.415
128.741
130.452
133.914
135.967
156.570
169.469
169.914
169.941
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
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100
.612
7611
MH
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3
2768
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9.8
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100
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MH
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====
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HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
94.6
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
3
000
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
0.4
0D
ate_
2
0140
904
PRO
CNO
1
EXPN
O
3N
AM
E
SM−D
127_
A
OAcOAcO
OAcO
CN
31
S37
1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (32)
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
ppm
2.0462.0572.122
3.4263.4473.4553.4774.2954.3074.3244.3374.9034.9104.9154.9244.9314.9364.9454.9574.9754.9955.0155.1815.2015.221
7.4727.4847.4857.4897.4957.4977.5037.5077.5097.5247.5287.5457.5507.7797.7937.8017.8097.8197.8327.9777.981
6.1003.058
1.014
1.007
2.0270.9871.003
2.992
3.0031.000
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0100
MH
zSI
13
1072
P1
9.8
0 us
ecN
UC1
1
HSF
O1
400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
293
.6 K
DE
6
.50
usec
DW
69
.333
use
cRG
7
1.8
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
SWH
7211
.539
Hz
DS
2N
S
8
SOLV
ENT
C
DCl
3TD
5
7690
PULP
ROG
zg30
PRO
BH
D
5 m
m P
AB
BO
BB
−IN
STRU
M
spe
ctTi
me
7.3
5D
ate_
2
0140
826
PRO
CNO
1
EXPN
O
1N
AM
E
SM−D
121_
C
OAcOAcO
OAc
S
32
S38
13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (32)
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
200
210
ppm
20.859
20.877
20.968
65.235
68.480
70.007
71.946
86.427
126.758
126.786
127.799
127.841
128.768
129.644
129.884
132.156
132.872
133.609
169.498
169.906
170.023
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
7582
MH
zSI
3
2768
P1
9.8
0 us
ecN
UC1
1
3CSF
O1
100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
94.0
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
1
000
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
8.0
2D
ate_
2
0140
826
PRO
CNO
1
EXPN
O
2N
AM
E
SM−D
121_
C
OAcOAcO
OAc
S
32
S39
1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl β-D-xylopyranosyl sulfone (33)
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
10.0
10.5
ppm
1.9922.0102.129
3.3413.3653.3703.3944.1924.2054.2214.2344.5434.5664.7684.7814.7914.8044.8144.8285.2245.2465.2685.2875.2995.310
7.6367.6397.6567.6737.6777.6967.6997.7177.7207.7347.7377.8627.8667.8837.8887.9507.9708.0028.0248.0378.0578.0678.499
3.0223.0472.926
1.000
1.009
0.982
0.989
1.0131.325
0.9801.0030.9721.0950.9791.131
0.961
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0101
MH
zSI
13
1072
P1
9.8
0 us
ecN
UC1
1
HSF
O1
400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
.3 K
DE
6
.50
usec
DW
69
.333
use
cRG
203
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
SWH
7211
.539
Hz
DS
2N
S
32
SOLV
ENT
C
DCl
3TD
5
7690
PULP
ROG
zg30
PRO
BH
D
5 m
m P
AB
BO
BB
−IN
STRU
M
spe
ctTi
me
9.2
3D
ate_
2
0140
911
PRO
CNO
1
EXPN
O
1N
AM
E
KT−
D08
8
OAcOAcO
OAc
S
OO
33
S40
13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl β-D-xylopyranosyl sulfone (33)
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
20.745
20.885
66.867
67.019
68.254
72.710
89.973
124.541
127.841
128.119
129.336
129.911
129.942
132.002
132.148
132.771
135.944
169.622
169.784
170.153
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
7553
MH
zSI
3
2768
P1
9.8
0 us
ecN
UC1
1
3CSF
O1
100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
94.6
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
4
500
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
4.4
5D
ate_
2
0140
912
PRO
CNO
1
EXPN
O
3N
AM
E
KT−
D08
8
OAcOAcO
OAc
S
OO
33
S41
1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl β-L-xylopyranoside (35)
13
12
11
10
98
76
54
32
1ppm
2.1002.1052.1133.5793.5983.6093.6284.2594.2704.2894.3015.0205.0315.0385.0505.0565.0695.2205.2345.2385.2515.2545.2565.2735.2925.3315.3467.1677.1737.1897.1957.3637.3687.3857.3887.3917.4057.4087.4417.4447.4587.4617.4647.4787.4827.7337.7537.7687.7807.7907.800
8.94
1.00
1.01
1.012.021.03
0.952.021.053.05
PC 4.00
GB 0
LB 0.30 Hz
SSB 0
WDW EM
SF 400.1300098 MHz
SI 131072
SFO1 400.1334011 MHz
PL1W 27.00716019 W
PL1
−5
.00
dBP1 9.10 usec
NUC1 1H
======== CHANNEL f1 ========
TD0 1
D1 0.00100000 sec
TE 300.0 K
DE 6.00 usec
DW 69.333 usec
RG 456
AQ 3.9998901 sec
FIDRES 0.125005 Hz
SWH 7211.539 Hz
DS 2
NS 32
SOLVENT CDCl3
TD 57690
PULPROG zg30
PROBHD 5 mm PABBO BB/
INSTRUM spect
Time 8.19
Date_ 20130809
PROCNO 1
EXPNO 1
NAME
K
H−B2
00b
OAcO
AcO
OOAc
35
S42
13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl β-L-xylopyranoside (35)
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
20.899
20.931
20.956
62.011
68.636
70.240
70.709
98.669
111.443
118.936
124.772
126.742
127.302
127.828
129.826
130.175
134.295
154.464
169.574
170.014
170.097
SF
100
.612
7546
MH
zSI
3
2768
SFO
2
4
00.1
3160
05 M
Hz
PL12
W
0
.349
5255
4 W
PL2W
27.
0071
6019
WPL
12
1
3.88
dB
PL2
−5.
00 d
BPC
PD2
80.0
0 us
ecN
UC2
1
HCP
DPR
G2
wal
tz16
====
====
CH
AN
NEL
f2 =
====
===
SFO
1
1
00.6
2282
98 M
Hz
PL1W
73.
8220
0623
WPL
1
−
4.00
dB
P1
8.0
0 us
ecN
UC1
1
3C==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
3
00.0
KD
E
6.0
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
8
000
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B/IN
STRU
M
spe
ctTi
me
22.
33D
ate_
2
0130
809
PRO
CNO
1
EXPN
O
3N
AM
E
KH
−B20
0b
OAcO
AcO
OOAc
35
S43
1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl 1-thio-α-L-arabinopyranoside (38)
109
87
65
43
21
ppm
2.0682.0862.128
3.6873.6923.7193.7244.1834.1944.2144.2254.9154.9345.1205.1295.1415.1495.2825.2885.2935.2985.3025.3075.3227.4667.4787.4817.4917.5017.5047.5167.5517.5567.5737.5777.7797.7907.7947.8017.8107.8157.8298.0038.008
3.0252.9533.061
1.000
1.023
0.9701.0072.016
2.0251.0243.0780.974
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0101
MH
zSI
13
1072
P1
9.8
0 us
ecN
UC1
1
HSF
O1
400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
.8 K
DE
6
.50
usec
DW
69
.333
use
cRG
181
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
SWH
7211
.539
Hz
DS
2N
S
32
SOLV
ENT
C
DCl
3TD
5
7690
PULP
ROG
zg30
PRO
BH
D
5 m
m P
AB
BO
BB
−IN
STRU
M
spe
ctTi
me
9.0
8D
ate_
2
0140
909
PRO
CNO
1
EXPN
O
1N
AM
E
KT−
D08
0
O
AcO
OAc
S
OAc
38
S44
13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl 1-thio-α-L-arabinopyranoside (38)
20
30
40
50
60
70
80
90
100
110
120
130
140
150
160
170
180
190
200
210
ppm
20.879
21.036
65.441
67.629
68.733
70.581
87.061
126.676
126.777
127.756
127.850
128.738
129.622
130.619
131.693
132.814
133.647
169.592
170.108
170.387
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
7561
MH
zSI
3
2768
P1
9.8
0 us
ecN
UC1
1
3CSF
O1
100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
95.1
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
9
000
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
22.
44D
ate_
2
0140
909
PRO
CNO
1
EXPN
O
3N
AM
E
KT−
D08
0
O
AcO
OAc
S
OAc
38
S45
1H-NMR 2-Naphthyl 2,3,4-tri-O-acetyl α-L-arabinopyranosyl sulfone (39)
109
87
65
43
21
ppm
1.637
1.9912.151
3.6623.6643.6943.6974.0764.0824.1094.1154.1274.5374.5605.0405.0485.0645.0725.1305.1375.1415.5035.5275.5507.6247.6277.6417.6447.6617.6657.6787.6827.6997.7027.7167.7197.9257.9307.9477.9517.9998.0218.0538.0738.557
3.171
3.2213.275
1.069
1.303
1.031
1.0801.048
1.029
2.1422.0681.1101.142
1.000
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0101
MH
zSI
13
1072
P1
9.8
0 us
ecN
UC1
1
HSF
O1
400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
.6 K
DE
6
.50
usec
DW
69
.333
use
cRG
181
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
SWH
7211
.539
Hz
DS
2N
S
32
SOLV
ENT
C
DCl
3TD
5
7690
PULP
ROG
zg30
PRO
BH
D
5 m
m P
AB
BO
BB
−IN
STRU
M
spe
ctTi
me
8.3
8D
ate_
2
0140
918
PRO
CNO
1
EXPN
O
1N
AM
E
KT−
D09
2
O
AcO
OAc
S
OO
OAc
39
S46
13C-NMR 2-Naphthyl 2,3,4-tri-O-acetyl α-L-arabinopyranosyl sulfone (39)
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
20.396
20.754
20.997
64.581
67.583
67.723
70.962
90.080
124.867
127.739
127.984
128.903
129.809
129.918
132.070
132.194
132.827
135.823
169.629
170.057
170.156
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
7555
MH
zSI
3
2768
P1
9.8
0 us
ecN
UC1
1
3CSF
O1
100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
95.4
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
3
072
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
21.
43D
ate_
2
0140
918
PRO
CNO
1
EXPN
O
3N
AM
E
KT−
D09
2
O
AcO
OAc
S
OO
OAc
39
S47
1H-NMR (2-Naphthyl)-methyl 2,3,4-tri-O-acetyl α-L-arabinopyranoside (40)
12
11
10
98
76
54
32
1ppm
2.0022.0312.1273.5903.5943.6223.6264.0394.0474.0714.0804.5094.5264.7324.7634.9945.0035.0165.0265.0455.2495.2545.2585.2625.2665.2745.2915.2975.3147.3937.3977.4147.4187.4447.4577.4597.4617.4697.4807.4827.4947.7457.7927.8067.8167.827
2.923.073.05
1.00
1.10
1.011.02
2.022.08
1.022.051.033.09
PC 4.00
GB 0
LB 0.30 Hz
SSB 0
WDW EM
SF 400.1300095 MHz
SI 131072
P1 9.80 usec
NUC1 1H
SFO1 400.1332010 MHz
======== CHANNEL f1 ========
TD0 1
D1 0.00100000 sec
TE 294.1 K
DE 6.50 usec
DW 69.333 usec
RG 25.4
AQ 3.9998901 sec
FIDRES 0.125005 Hz
SWH 7211.539 Hz
DS 2
NS 32
SOLVENT CDCl3
TD 57690
PULPROG zg30
PROB
HD
5 m
m PA
BBO
BB−
INSTRUM spect
Time 16.37
Date_ 20140825
PROCNO 1
EXPNO 1
NAME
K
T−D0
58d
O
AcO
OAcO
OAc
40
S48
13C-NMR (2-Naphthyl)-methyl 2,3,4-tri-O-acetyl α-L-arabinopyranoside (40)
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
14.116
20.652
20.782
20.898
22.665
31.846
63.039
67.603
69.176
70.102
70.363
99.433
125.481
126.066
126.253
126.507
127.710
127.826
128.209
132.995
133.143
134.429
169.417
170.066
170.289
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
7729
MH
zSI
3
2768
P1
9.8
0 us
ecN
UC1
1
3CSF
O1
100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
94.5
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
9
000
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
0.4
1D
ate_
2
0140
826
PRO
CNO
1
EXPN
O
3N
AM
E
KT−
D05
8d
O
AcO
OAcO
OAc
40
S49
1H-NMR 5-Chloro-3-oxo-1-pentyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside (42)
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
ppm
2.0722.1323.5973.5993.6123.6153.6213.6273.6503.6543.6653.6723.6823.6843.6913.6983.7053.7263.7333.7403.7493.7533.7563.9263.9353.9443.9513.9583.9633.9714.0094.0184.0424.0504.5004.5175.0195.0285.0435.0515.1735.1905.1975.2145.2485.2525.2565.2615.2655.269
3.223.123.30
8.30
1.031.03
1.00
1.021.021.02
PC 4.00
GB 0
LB 0.30 Hz
SSB 0
WDW EM
SF 400.1300101 MHz
SI 131072
P1 9.80 usec
NUC1 1H
SFO1 400.1332010 MHz
======== CHANNEL f1 ========
TD0 1
D1 0.00100000 sec
TE 293.8 K
DE 6.50 usec
DW 69.333 usec
RG 161
AQ 3.9998901 sec
FIDRES 0.125005 Hz
SWH 7211.539 Hz
DS 2
NS 32
SOLVENT CDCl3
TD 57690
PULPROG zg30
PROB
HD
5 m
m PA
BBO
BB−
INSTRUM spect
Time 10.54
Date_ 20140825
PROCNO 1
EXPNO 1
NAME
K
T−D0
56f
O
AcO
OAc
OAc
OO
Cl
42
S50
13C-NMR 5-Chloro-3-oxo-1-pentyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside (42)
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
20.830
20.963
21.078
42.975
63.332
67.797
68.826
69.246
70.314
70.507
71.550
101.132
169.668
170.316
170.479PC
1
.40
GB
0LB
1
.00
Hz
SSB
0W
DW
EMSF
1
00.6
1275
64 M
Hz
SI
327
68P1
9
.80
usec
NU
C1
13C
SFO
1
1
00.6
2282
98 M
Hz
====
====
CH
AN
NEL
f1 =
====
===
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
94.9
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
9
000
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
23.
43D
ate_
2
0140
822
PRO
CNO
1
EXPN
O
3N
AM
E
KT−
D05
6c
O
AcO
OAc
OAc
OO
Cl
42
S51
1H-NMR 5-(2-Naphthoxy)-3-oxo-1-pentyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside (43)
109
87
65
43
21
ppm2.014
2.0412.1133.5603.5643.5923.5973.7263.7323.7363.7433.7523.7603.8833.8843.8953.8993.9083.9613.9703.9763.9853.9883.9934.0174.0264.2094.2164.2214.2334.4884.5055.0085.0175.0315.0405.1855.2025.2085.2265.2305.2345.2395.2435.2477.1347.1407.1587.1647.1807.1867.3097.3237.3267.3297.3437.3467.4077.4107.4247.4277.4317.4457.4487.7087.7237.7287.745
3.0822.9592.916
1.0423.0512.0312.0751.992
0.991
1.0591.0060.981
0.9920.9751.0061.0002.979
PC
4.0
0G
B
0
LB
0.3
0 H
zSS
B
0
WD
W
EM
SF
400
.130
0099
MH
zSI
13
1072
P1
9.8
0 us
ecN
UC1
1
HSF
O1
400
.133
2010
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
1
0.0
0100
000
sec
TE
294
.7 K
DE
6
.50
usec
DW
69
.333
use
cRG
4
0.3
AQ
3.99
9890
1 se
cFI
DRE
S
0
.125
005
Hz
SWH
7211
.539
Hz
DS
2N
S
32
SOLV
ENT
C
DCl
3TD
5
7690
PULP
ROG
zg30
PRO
BH
D
5 m
m P
AB
BO
BB
−IN
STRU
M
spe
ctTi
me
15.
15D
ate_
2
0140
827
PRO
CNO
1
EXPN
O
1N
AM
E
KT−
D06
0
O
AcO
OAc
OAc
OO
O
43
S52
13C-NMR 5-(2-Naphthoxy)-3-oxo-1-pentyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside (43)
210
200
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
ppm
20.741
20.841
20.980
63.186
67.477
67.733
68.868
69.192
69.906
70.240
70.629
101.102
106.749
119.010
123.754
126.441
126.807
127.703
129.083
129.492
134.529
156.756
169.624
170.218
170.388
PC
1.4
0G
B
0
LB
1.0
0 H
zSS
B
0
WD
W
EM
SF
100
.612
7649
MH
zSI
3
2768
P1
9.8
0 us
ecN
UC1
1
3CSF
O1
100
.622
8298
MH
z==
====
== C
HA
NN
EL f1
===
====
=
TD0
1D
11
0.0
3000
000
sec
D1
0
.001
0000
0 se
cTE
2
95.0
KD
E
6.5
0 us
ecD
W
20.8
00 u
sec
RG
5
7A
Q
0.
9999
892
sec
FID
RES
0.5
0003
0 H
zSW
H
240
38.4
61 H
zD
S
4
NS
9
000
SOLV
ENT
C
DCl
3TD
4
8074
PULP
ROG
z
gdc3
0PR
OBH
D
5 m
m P
ABB
O B
B−IN
STRU
M
spe
ctTi
me
22.
45D
ate_
2
0140
827
PRO
CNO
1
EXPN
O
3N
AM
E
KT−
D06
0
O
AcO
OAc
OAc
OO
O
43