Table 2.
1H (500 MHz) and 13C (125 MHz) NMR data of 7–11 (δH in ppm, J in Hz)
| No | 7a | 8a | 9b | 10a | 11a | |||||
|---|---|---|---|---|---|---|---|---|---|---|
| δH (J in Hz) | δC, type | δH (J in Hz) | δC, type | δH (J in Hz) | δC, type | δH (J in Hz) | δC, type | δH (J in Hz) | δC, type | |
| 1 | 6.80, s | 96.8, CH | 6.77, s | 97.1, CH | 6.93, s | 97.4, CH | 7.46, d (8.3) | 110.8, CH | 7.38, d (8.0) | 110.6, CH |
| 2 | 152.5, C | 152.4, C | 154.7, C | 7.89, d (8.3) | 126.5, CH | 7.35, d (8.0) | 124.4, CH | |||
| 3 | 116.3, C | 116.1, C | 117.3, C | 129.4, C | 132.6, C | |||||
| 4 | 7.77, s | 121.3, CH | 7.66, s | 121.2, CH | 7.65, s | 121.5, CH | 8.48, s | 123.0, CH | 7.94, s | 118.7, CH |
| 4a | 117.8, C | 118.1, C | 117.6, C | 124.4, C | 124.3, C | |||||
| 4b | 118.7, C | 118.2, C | 119.1, C | 117.3, C | 117.5, C | |||||
| 5 | 8.24, s | 113.6, CH | 7.73, d (8.4) | 117.9, CH | 7.70, d (8.4) | 117.5, CH | 7.83, d (8.3) | 119.3, CH | 7.77, d (8.4) | 120.7, CH |
| 6 | 116.1, C | 6.81, d (8.4) | 104.1, CH | 6.82, d (8.4) | 105.0, CH | 6.83, d (8.3) | 110.7, CH | 6.74, d (8.4) | 110.0, CH | |
| 7 | 151.6, C | 155.4, C | 155.6, C | 153.3, C | 152.1, C | |||||
| 8 | 6.91, s | 99.3, CH | 109.4, C | 112.3, C | 109.2, C | 104.8, C | ||||
| 9 | 7.76, br s | 8.48, br s | 9.55, br s | 8.29, br s | 7.96, br s | |||||
| 8a | 140.9, C | 141.8, C | 141.0, C | 140.9, C | 136.8, C | |||||
| 9a | 139.7, C | 140.2, C | 141.4, C | 143.6, C | 139.3, C | |||||
| 1′ | 129.9, C |
2.91, dd (14.3, 8.4) 3.34, dd (14.3, 2.5) |
32.4, CH2 | 3.61, d (6.6) | 24.6, CH2 | 3.65, d (7.0) | 24.4, CH2 | 6.66, d (9.8) | 117.3, CH | |
| 2′ | 7.69, br s | 122.8, CH | 4.41, dd (8.4, 2.5) | 76.1, CH | 5.36, d (6.6) | 123.4, CH | 5.39, t (7.0) | 121.2, CH | 5.68, d (9.8) | 129.0, CH |
| 3′ | 137.4, C | 152.3, C | 136.3, C | 139.2, C | 78.6, C | |||||
| 4′ | 7.08, d (7.9) | 127.6, CH | 4.91, s; 5.13, s | 108.9, CH2 | 1.83, s | 16.5, CH3 | 1.91, s | 16.7, CH3 | 1.46, s | 26.2, CH3 |
| 5′ | 7.16, d (7.9) | 123.2, CH | 2.23, m | 32.6, CH2 | 2.01, m; 2.35, m | 37.8, CH2 | 2.10‒2.15, m | 39.8, CH2 | 1.76, m | 41.0, CH2 |
| 6′ | 136.5, C | 2.23, m | 26.8, CH2 | 1.31, m; 1.67, m | 30.8, CH2 | 2.10‒2.15, m | 26.6, CH2 | 2.17, m | 22.9, CH2 | |
| 7′ | 77.8, C | 5.18, t (6.6) | 124.2, CH | 3.23, d (10.9) | 78.6, CH | 5.06, m | 123.8, CH | 5.11, t (7.5) | 124.2, CH | |
| 8′ | 1.64, s | 27.7, CH3 | 132.1, C | 72.8, C | 132.3, C | 131.9, C | ||||
| 9′ | 1.64, s | 27.7, CH3 | 1.64, s | 17.9, CH3 | 1.08, s | 25.2, CH3 | 1.59, s | 17.9, CH3 | 1.58, s | 17.8, CH3 |
| 10′ | 1.71, s | 25.9, CH3 | 1.08, s | 25.9, CH3 | 1.64, s | 25.8, CH3 | 1.66, s | 25.8, CH3 | ||
| 3-CH3 | 2.41, s | 16.3, CH3 | 2.38, s | 16.3, CH3 | 2.32, s | 16.7, CH3 | ||||
| 3′-CH3 | 2.45, s | 21.6, CH3 | ||||||||
| 3-CHO | 10.07, s | 192.2, CH | ||||||||
| 3-CH2OH | 4.83, s | 66.3, CH2 | ||||||||
| 7-OCH3 | 3.90, s | 56.5, CH3 | 3.87, s | 56.9, CH3 | ||||||
aMeasured in CDCl3
bMeasured in acetone-d6