synthesis of “dihydroacarbose”, a potent α-d-glucosidase inhibitor

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hydrate er Scien dam - Printed in nolate-acetone.

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Page 1: Synthesis of “dihydroacarbose”, a potent α-d-glucosidase inhibitor

hydrate er Scien dam - Printed in

nolate-acetone.

Page 2: Synthesis of “dihydroacarbose”, a potent α-d-glucosidase inhibitor

c6 PRELI YCO

I) R = R’Z R”Z” P x =1.x’ =OHk,

6 R = R’Z F/‘= .4c ,0x = H,X’=*N,n) 7 R = Bn,R’,R-= PnCH (I x = H,d = I (0)

(I R = B”,R’ = R”Z ” c

$1 x = G-3.X’ = N1 tf21

13 x = H,X’ = NH~Iel

- + I, - 0

6” ii R OR

B”0

16R = H ,7R = H

86R = 81 lI)R = 82

Page 3: Synthesis of “dihydroacarbose”, a potent α-d-glucosidase inhibitor

P YCO c7

13 + 19 - + I”‘-# 1acmer

21

RO RO RO RO

toid = B”,R = -ir (20:22= is:11

21 R = d=4c

Page 4: Synthesis of “dihydroacarbose”, a potent α-d-glucosidase inhibitor

C U~ICAT~O~

ibi~ion (IC,, 1.2 X lo-6M) of sucrase

1 E. TRUSCHE~, W. FROMMER, B. JLJNGE, L. MILLER, D. D. SCHMIDT. AND W. WINGEN~ER, Angew. ein., Inc. Ed. Engl., 20 (19

2 JUNGE, F.-R. HEIKER, J. SCHMIDT. AND C. WUNSCHE, Carbobydr. Res., 128 (1984) 235-268.

JUNGE AND L. OLLER, Ger. O~e~. DE 3123520 (1982): Chem. Abstr., 98 (1983) 198,655g. SAKAIRI AND H. UZUHARA, TetrQbedron Lett., (19 2) 5327-5330~ (b) S. OGAWA, H.

SUGIZAKI, 5’. IWASAWA. AND T. SUAMI, Carbohydr. Res., 140 (1985) 325-331; (c) S.

5 I. FUJIMAKI, Y. ICH~KAWA AND 6 K. TAKEO AND T. 7 8 9

10 A~tibiot., 34 (19~1) ~42~1433.