Table 1.
One-dimensional nuclear magnetic resonance (1D-NMR) spectroscopic data for compounds 1–4 (in CDCl3).
| 1 | 2 | 3 | 4 | |||||
|---|---|---|---|---|---|---|---|---|
| No | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) |
| 2 | 84.3, C | – | 85.3, C | – | 84.5, C | – | 85.5, C | – |
| 3 | 71.8, CH | 4.25, dd (12.3, 5.3) | 71.7, CH | 4.46, dd (12.3, 5.0) | 66.9, CH | 4.49, dd (4.0, 2.0) | 68.6, CH | 4.74, dd (12.7, 5.1) |
| 4 | 23.7, CH2 | 2.15, m, Ha 2.08, m, Hb |
23.9, CH2 | 2.21, m, Ha 2.10, m, Hb |
22.9, CH2 | 2.18, m, Ha 2.00, m, Hb |
32.7, CH2 | 2.42, m, Ha 2.23, m, Hb |
| 5 | 27.5, CH2 | 2.65, m | 27.7, CH2 | 2.69, m | 24.4, CH2 | 2.84, m 2.44, m |
65.9, CH | 4.55, d (4.7) |
| 6 | 178.1, C | – | 178.5, C | – | 180.2, C | – | 174.0, C | – |
| 7 | 101.1, C | – | 101.6, C | – | 100.2, C | – | 101.8, C | – |
| 8 | 186.5, C | – | 186.7, C | – | 186.9, C | – | 188.0, C | – |
| 9 | 104.9, C | – | 105.4, C | – | 105.3, C | – | 105.8, C | – |
| 10 | 156.8, C | – | 160.1, C | – | 160.2, C | – | 160.1, C | – |
| 11 | 117.3, C | – | 114.2, CH | 6.13, s | 114.7, CH | 6.15, s | 114.3, CH | 6.14, s |
| 12 | 147.8, C | – | 147.6, C | – | 147.3, C | – | 148.5, C | – |
| 13 | 110.9, CH | 6.07, s | 115.3, C | – | 115.2, C | – | 115.5, C | – |
| 14 | 158.4, C | – | 154.8, C | – | 153.6, C | – | 155.0, C | – |
| 15 | 169.6, C | – | 169.8, C | – | 171.0, C | – | 169.2, C | – |
| 1′ | 72.8, CH | 5.96, s | 72.7, CH | 5.98, s | 72.7, CH | 5.98, s | 72.7, CH | 5.98, s |
| 2′ | 136.6, C | – | 136.5, C | – | 136.6, C | – | 136.5, C | – |
| 3′ | 123.1, CH | 6.89, s | 123.2, CH | 6.90, s | 123.2, CH | 6.90, s | 123.3, CH | 6.90, s |
| 4′ | 147.6, C | – | 147.7, C | – | 147.8, C | – | 147.8, C | – |
| 5′ | 119.3, CH | 6.81, s | 119.3, CH | 6.80, s | 119.3, CH | 6.80, s | 119.4, CH | 6.80, s |
| 6′ | 161.7, C | – | 161.6, C | – | 161.7, C | – | 161.5, C | – |
| 7′ | 112.7, C | – | 112.4, C | – | 112.6, C | – | 112.3, C | – |
| 8′ | 185.8, C | – | 185.3, C | – | 185.2, C | – | 184.8, C | – |
| 9′ | 105.5, C | – | 105.6, C | – | 105.7, C | – | 105.6, C | – |
| 10′ | 186.0, C | – | 186.1, C | – | 186.4, C | – | 186.4, C | – |
| 11′ | 37.3, CH | 4.76, dd (6.6, 1.0) | 38.6, CH | 4.81, dd (6.7, 0.7) | 37.9, CH | 4.76, dd (6.7, 1.0) | 38.7, CH | 4.83, dd (6.6, 0.9) |
| 12′ | 131.9, CH | 6.42, dd (8.5, 6.6) | 131.8, CH | 6.48, dd (8.4, 6.7) | 131.6, CH | 6.41, dd (8.4, 6.7) | 131.7, CH | 6.47, dd (8.4, 6.6) |
| 13′ | 132.4, CH | 6.05, dd (8.5, 1.0) | 132.3, CH | 6.08, dd (8.4, 0.7) | 132.7, CH | 6.07, dd (8.4, 1.0) | 132.4, CH | 6.08, d (8.4, 0.9) |
| 14′ | 41.5, C | – | 41.6, C | 41.4, C | – | 41.6, C | – | |
| 15′ | 35.1, CH2 | 2.74, d (18.5), Ha 2.68, d (18.5), Hb |
35.0, CH2 | 2.79, d (18.0), Ha 2.67, d (18.0), Hb |
35.0, CH2 | 2.78, d (17.9), Ha 2.68, d (17.9), Hb |
35.1, CH2 | 2.80, d (18.0), Ha 2.69, d (18.0), Hb |
| 16′ | 22.0, CH3 | 2.38, s | 22.1, CH3 | 2.38, s | 22.1, CH3 | 2.38, s | 22.1, CH3 | 2.38, s |
| 18′ | 173.1, C | – | 173.1, C | – | 173.0, C | – | 173.1, C | – |
| 19′ | 36.2, CH2 | 2.22, m | 36.2, CH2 | 2.23, m | 36.2, CH2 | 2.22, m | 36.2, CH2 | 2.22, m |
| 20′ | 18.4, CH2 | 1.57, m | 18.4, CH2 | 1.58, m | 18.4, CH2 | 1.57, m | 18.4, CH2 | 1.57, m |
| 21′ | 13.5, CH3 | 0.86, t (7.4) | 13.5, CH3 | 0.86, t (7.4) | 13.5, CH3 | 0.86, t (7.4) | 13.5, CH3 | 0.86, t (7.4) |
| 15- OCH3 | 53.4, CH3 | 3.67, s | 53.3, CH3 | 3.73, s | 53.6, CH3 | 3.74, s | 53.4, CH3 | 3.73, s |
| 3-OH | – | 14.14 | – | 14.26 | – | – | – | – |
| 6-OH | – | 13.84 | – | 13.95 | – | 14.10 | – | 13.70 |
| 10-OH | – | 11.76 | – | 11.05 | – | 11.24 | – | 10.91 |
| 6′-OH | – | 11.58 | – | 11.40 | – | 11.55 | – | 11.30 |