Table 2.
1H (400 MHz) and 13C NMR (100 MHz) Spectroscopic Data of 5, 6, and 9 (CDCl3)a
| 5 | 6 | 9 | ||||
|---|---|---|---|---|---|---|
| carbon | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) |
| 1 | 152.6 | 152.9 | 187.7 | |||
| 2 | 108.6 | 6.27, s | 118.6 | 141.2 | ||
| 3 | 133.8 | 135.1 | 146.3 | |||
| 4 | 131.4 | 131.2 | 184.7 | |||
| 5 | 146.4 | 146.1 | 154.3 | |||
| 6 | 113.0 | 102.8 | 6.28, s | 107.8 | 6.04, s | |
| 1′ | 30.4 | 2.40, t (7.6) | 27.7 | 2.42, t (7.2) | 26.7 | 2.48, t (7.8) |
| 2′ | 29.7 | 1.52, m | 30.0 | 1.40, m | 29.0 | 1.49, m |
| 3′ | 31.8 | 1.30, m | 32.4 | 1.31, m | 32.4 | 1.33, m |
| 4′ | 22.6 | 1.30, m | 22.6 | 1.31, m | 22.6 | 1.33, m |
| 5′ | 14.2 | 0.88, t (6.8) | 14.3 | 0.88, t (6.4) | 14.1 | 0.89, t (6.8) |
| 1″ | 23.1 | 3.40, d (7.6) | 25.3 | 3.26, d (6.0) | 25.8 | 3.21, d (6.8) |
| 2″ | 123.9 | 5.04, t (7.6) | 123.3 | 5.09, t (6.0) | 119.9 | 4.93, t (6.8) |
| 3″ | 139.5 | 136.5 | 137.5 | |||
| 4″ | 39.9 | 2.05, m | 39.9 | 1.98, m | 40.0 | 1.97, m |
| 5″ | 26.5 | 2.10, m | 26.7 | 2.06, m | 26.5 | 2.05, m |
| 6″ | 121.6 | 5.27, t (6.4) | 124.3 | 5.04, t (6.4) | 124.2 | 5.03, t (6.8) |
| 7″ | 132.4 | 131.8 | 131.7 | |||
| 8″ | 17.9 | 1.59, s | 17.9 | 1.57, s | 17.9 | 1.57, s |
| 9″ | 25.9 | 1.67, s | 25.9 | 1.65, s | 25.8 | 1.65, s |
| 10″ | 16.4 | 1.79, s | 16.4 | 1.75, s | 16.6 | 1.73, s |
| OCOCH3 | 20.8 | 2.33, s | 20.8 | 2.28, s | ||
| OCOCH3 | 170.1 | 170.0 | ||||
a
Assignments confirmed by DEPT-135, HMQC, COSY, and HMBC NMR experiments.