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Table 1 1 H- and 13 C-NMR Chemical Shifts of New Compounds 2–5 (δ in ppm; J and W 1 / 2 in Hz)

From: Synthesis of some potent immunomodulatory and anti-inflammatory metabolites by fungal transformation of anabolic steroid oxymetholone

Position

2

3

4

5

 

1H

13C

1H

13C

1H

13C

1H

13C

1

6.48, s

152.4

1.63; 1.57, m

36.5

2.28, dd (12.5, 4.5); 1.30, m

46.6

7.45, s

150.0

2

-

137.5

1.98, m

40.5

4.05, m (W1/2 = 20.6 )

73.1

-

137.6

3

-

199.0

4.51, br. s (W1/2 12.0)

67.6

3.86, m (W1/2 = 20.6 )

76.7

-

186.0

4

2.47, dd (17.3, 4.2), 2.26, dd (17.3, 4.0)

41.6

1.71; 1.60 m

37.7

1.87 ddd (13.0, 5.0, 2.5); 1.72, m

37.2

6.28, s

124.0

5

1.83, m

44.8

2.01, m

39.6

1.26, m

45.3

-

169.4

6

1.32; 1.27, m

27.6

1.31; 1.25, m

28.8

1.28; 1.22, m

28.4

2.32, 2.21, m

32.5

7

1.71; 0.85, m

31.5

1.65; 0.90, m

32.4

1.65; 0.85, m

32.2

1.75; 0.85, m

33.7

8

1.44, m

36.7

1.44, m

36.4

1.37, m

35.9

1.57, m

36.3

9

0.78, m

50.7

0.76, m

54.9

0.67, m

54.7

0.81, m

52.9

10

-

38.9

-

36.6

-

37.6

 

43.5

11

1.63; 1.37, m

21.3

1.57; 1.29, m

21.0

1.62; 1.33, m

21.4

1.65; 1.55, m

22.9

12

1.61; 1.22, m

32.2

1.78; 1.49, m

32.7

1.58, 1.35, m

32.0

1.53; 1.14, m

31.8

13

-

46.3

-

46.1

-

46.2

-

46.2

14

1.20, m

51.2

1.37, m

51.8

1.24, m

51.0

1.12, m

50.2

15

1.53; 1.24, m

23.7

1.57; 1.34, m

24.2

1.54; 1.29, m

23.8

1.48; 1.30, m

23.8

16

2.14, ddd (13.5, 11.7, 3.5); 1.77, m

39.5

2.30, ddd (15.6, 9.2, 6.7); 1.95, m

34.1

2.13; 1.76, m

39.4

2.14, td (13.0, 3.5); 1.78, m;

39.2

17

-

80.5

-

83.2

-

80.6

-

80.3

18

1.08, s

14.9

1.14, s

15.2

1.06, s

14.8

1.08, s

14.8

19

0.96, s

13.1

0.87, s

12.5

0.89, s

13.7

1.15, s

18.8

20

1.41. s

26.8

4.09; 3.82, d (10.3)

67.3

1.40, s

26.7

1.37, s

26.6

21

4.78; 4.76, d (15.0)

59.8

4.17; 4.03, m

66.1

-

-

5.06; 4.98, m

59.5