Table 1.
position | 1 (methanol-d4) | 2 (methanol-d4) | 4 (methanol-d4) | |||
---|---|---|---|---|---|---|
1H | 13C | 1H | 13C | 1H | 13C | |
1 | 7.24 s | 127.9 | 7.23 s | 127.7 | 7.31 s | 128.1 |
1a | 113.8 b | 113.7 | 113.8 | |||
2 | 121.8 b | 122.0 | 122.0 | |||
3 | 162.2 | 162.4 | 162.3 | |||
4 | 6.29 s | 98.7 | 6.27 s | 98.5 | 6.28 s | 98.5 |
4a | 157.3 | 157.4 | 157.5 | |||
6 | 4.22 dd (10.7, 4.6) 3.57 t (10.7) |
67.5 | 4.23 dd (10.7, 4.6) 3.56 t (10.7) |
67.5 | 4.22 dd (10.7, 3.6) (6α) 3.55 t, (10.7) (6β) |
67.6 |
6a | 3.49 ddd (10.7, 7.0, 4.6) | 41.5 | 3.49 ddd (10.7, 7.0, 4.6) | 41.4 | 3.51 m | 41.4 |
6b | 121.8 b | 120.9 | 120.5 | |||
7 | 6.81 s | 106.0 | 6.81 s | 105.9 | 6.74 d, (8.1) | 115.4 |
8 | 143.2b | 143.6 | 6.50 d (8.1) | 105.8 | ||
9 | 149.4 b | 149.3 | 150.2 | |||
10 | 6.37 s | 94.2 | 6.37 s | 94.1 | 131.7 | |
10a | 155.5 b | 155.4 | 156.4 | |||
11a | 5.47 d (7.0) | 80.3 | 5.47 d (7.0) | 80.3 | 5.49 d (6.3) | 80.6 |
1′ | 3.07 dd (14.9, 7.5) 3.37 m |
35.3 | 2.98 dd (14.9, 7.5) 3.33 overlapped |
34.7 | 3.31 m 2.99 dd, (15.3, 7.8) |
34.8 |
2′ | 5.31 t (7.5) | 85.4 | 5.20 t (7.5) | 87.8 | 5.20 t (8.75) | 87.9 |
3′ | 143.2 b | 145.6 | 145.8 | |||
4′ | 4.15 s | 62.6 | 1.75 s | 17.1 | 1.75 s | 17.2 |
5′ | 5.21 br s | 110.8 | 5.05 br s | 112.0 | 5.05 brs | 112.1 |
-OCH2O- | 5.85 d (1.2) 5.88 d (1.2) |
102.5 | 5.85 br d (0.8) 5.88 br d (0.8) |
102.4 | ||
OCH3 | 3.82 s | 56.9 |
All assignment were based on the COSY, HSQC and HMBC experiments
The 13C NMR shifts of C-1a, C-2, C-6b, C-8, C-9, C-10a and C-3′ for compound 1 were observed by HMBC.