9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 … · 2018. 4. 20. · 9.5...

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

0.98

1.70

1.72

1.73

4.33

4.34

4.36

7.26

8.22

9.2

1

2.0

4

2.0

0

0.8

8

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

29.81

29.94

41.58

67.54

76.84

77.16

77.48

91.77

163.28

Electronic Supplementary Material (ESI) for Chemical Science.This journal is © The Royal Society of Chemistry 2018

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

0.88

0.90

0.92

0.94

1.37

1.39

1.40

1.41

1.42

1.43

1.76

1.78

1.80

4.27

4.29

4.30

7.26

8.22

3.4

1

4.2

6

2.0

7

2.0

0

0.9

4

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

0.90

1.28

1.29

1.31

1.32

1.33

1.34

1.35

1.36

1.42

1.44

1.45

1.46

1.74

1.76

1.77

1.78

1.79

4.27

4.29

4.30

7.26

8.22

2.9

4

8.4

0

2.1

5

2.1

5

1.9

9

0.9

0

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

14.17

22.74

25.96

28.39

29.29

31.90

69.78

76.95

77.16

77.37

91.86

163.19

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.14

1.15

1.16

1.19

1.20

1.22

1.23

1.26

1.27

1.29

1.30

1.31

1.33

1.62

1.66

1.67

1.69

1.72

1.73

1.75

1.77

1.78

1.80

4.24

4.25

4.27

7.26

8.21

2.1

3

6.1

7

7.4

0

2.0

0

0.9

4

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

25.71

26.40

26.72

33.37

33.52

37.33

69.96

76.94

77.16

77.37

91.82

162.97

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.76

1.77

1.78

1.79

1.80

1.81

1.82

1.83

1.84

1.85

2.67

2.69

2.70

4.30

4.31

4.32

7.18

7.19

7.20

7.26

7.27

7.28

7.30

8.24

4.3

0

2.0

8

2.0

0

3.0

1

2.1

3

0.9

1

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

0.90

1.28

1.29

1.31

1.32

1.33

1.34

1.35

1.36

1.42

1.44

1.45

1.46

1.74

1.76

1.77

1.78

1.79

4.27

4.29

4.30

7.26

8.22

2.9

4

8.4

0

2.1

5

2.1

5

1.9

9

0.9

0

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

31.45

41.21

66.03

76.84

77.16

77.48

91.48

162.81

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

1.47

1.48

1.49

1.51

1.52

1.55

1.56

1.58

1.59

1.60

1.78

1.79

1.80

1.81

1.82

3.61

3.63

3.64

4.29

7.26

8.22

6.0

4

9.1

2

2.1

9

2.1

2

2.0

5

2.0

1

2.0

0

0.8

7

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

-5.17

18.43

22.43

26.08

28.23

32.48

63.01

69.64

76.95

77.16

77.37

91.80

163.11

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.21

2.11

2.13

2.14

4.22

4.39

7.26

8.31

9.1

4

2.0

5

2.0

2

2.0

0

0.8

9

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

27.26

27.82

38.83

60.77

65.92

76.95

77.16

77.37

91.48

162.83

178.36

11 10 9 8 7 6 5 4 3 2 1 ppm

1.81

2.38

2.39

2.41

3.67

4.29

4.30

4.32

7.26

8.26

4.4

0

2.1

4

3.1

3

2.0

0

0.9

9

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

21.50

27.80

33.57

51.64

69.05

76.84

77.16

77.47

91.60

162.98

173.77

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.84

1.85

3.74

3.76

3.77

4.32

7.26

7.70

7.71

7.72

7.83

7.84

7.85

8.25

4.1

9

2.0

0

2.0

1

2.1

4

2.1

6

0.9

6

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

25.34

25.93

37.70

68.90

76.95

77.16

77.37

91.65

123.38

132.29

134.07

163.02

168.50

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

9.48

25.91

76.95

77.16

77.38

82.01

92.36

162.77

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5 ppm

1.30

1.34

1.36

2.07

2.08

2.10

2.11

2.35

2.36

2.39

2.40

5.16

5.17

5.18

7.26

8.29

3.1

1

2.9

6

2.9

5

3.1

2

1.0

2

1.0

5

1.0

0

0.9

9

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.15

1.17

1.19

1.21

1.30

1.32

1.33

1.34

1.35

1.37

1.38

1.62

1.64

1.65

1.70

1.90

1.92

2.41

2.42

4.65

7.26

8.47

3.3

5

3.3

9

3.4

5

2.1

5

2.0

9

2.0

0

1.0

9

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

2.58

2.60

2.62

2.92

2.94

2.96

4.79

7.22

7.24

7.26

7.29

7.31

8.52

2.0

6

2.2

0

2.0

0

3.2

1

2.6

1

0.9

8

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

6.29

37.97

52.83

76.95

77.16

77.38

80.53

91.06

126.59

128.79

139.51

161.35

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

4.26

4.69

7.26

8.53

2.0

1

2.0

1

0.8

3

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

-0.52

56.64

76.48

76.95

77.16

77.37

90.88

160.91

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm

0.06

0.89

1.84

1.85

1.86

1.87

1.88

1.89

2.34

2.35

2.36

3.71

3.72

3.73

4.75

7.26

8.48

6.1

7

9.3

2

2.2

7

2.2

4

2.1

7

2.0

0

1.0

8

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

-5.10

8.19

18.43

26.11

35.16

47.96

61.54

76.95

77.16

77.37

80.97

91.06

161.38

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.26

4.54

4.72

7.26

8.51

8.9

2

1.9

8

2.0

0

0.9

8

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

-3.05

27.36

39.18

72.81

76.95

77.16

77.38

90.87

161.24

176.49

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

2.69

2.70

2.71

4.01

4.02

4.04

4.78

7.26

7.71

7.72

7.83

7.84

7.85

8.51

2.1

5

2.1

9

2.0

0

2.1

6

2.1

1

0.9

9

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

-1.52

40.52

48.09

76.94

77.16

77.37

80.61

90.90

123.52

132.16

134.21

161.21

168.01

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.59

1.60

3.02

4.61

4.62

4.63

4.64

7.26

8.50

3.0

4

3.0

6

1.0

0

1.0

0

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

5.35

19.19

43.55

76.95

77.16

77.37

84.24

91.23

160.99

COSY

NOESY

Hb

Ha

Hc

Hb

Ha

Hc

Hc Hd

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.37

4.87

7.26

8.47

9.0

4

2.0

0

0.9

1

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

27.92

27.97

44.05

75.58

76.95

77.16

77.37

83.51

91.06

162.16

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm

1.11

4.05

4.06

4.07

4.39

4.40

4.42

4.65

4.66

4.67

4.68

7.26

8.35

9.2

9

0.9

9

1.0

0

1.0

0

0.9

6

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 ppm

27.26

27.82

38.83

60.77

65.92

76.95

77.16

77.37

91.48

162.83

178.36

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 … · 2018. 4. 20. · 9.5...

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