Table 2.
1H and 13C NMR Data for 3–5 in D2O.
| No. | 3 a,c | 4 a,c | 5 b,c | 7 [11] | |||
|---|---|---|---|---|---|---|---|
| δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | |
| A1α | 94.7, CH | 5.23, d (3.5) | 94.8, CH | 5.23, d (3.5) | 94.8, CH | 5.24, d (3.5) | 93.0 |
| A2α | 74.2, CH | 3.58, m | 74.1, CH | 3.58, m | 74.2, CH | 3.58, m | 72.6 |
| A3α | 76.0, CH | 3.98, m | 76.0, CH | 3.98, m | 76.0, CH | 3.98, m | 74.4 |
| A4α | 79.5, CH | 3.66, m | 79.6, CH | 3.66, m | 79.5, CH | 3.67, m | 79.3 |
| A5α | 72.8, CH | 3.94, m | 72.8, CH | 3.94, m | 72.8, CH | 3.95, m | 71.0 |
| A6α | 63.3, CH2 | 3.84, m | 63.2, CH2 | 3.84, m | 63.2, CH2 | 3.84, m | 61.5 |
| A1β | 98.6, CH | 4.66, d (8.0) | 98.6, CH | 4.66, d (8.0) | 98.6, CH | 4.66, d (8.0) | 96.8 |
| A2β | 76.9, CH | 3.28, dd (9.5, 8.0) | 76.9, CH | 3.28, dd (9.5, 8.0) | 76.9, CH | 3.28, dd (9.5, 8.0) | 75.1 |
| A3β | 79.1, CH | 3.77, m | 79.0, CH | 3.78, m | 79.1, CH | 3.78, m | 77.3 |
| A4β | 79.6, CH | 3.66, m | 79.7, CH | 3.66, m | 79.6, CH | 3.66, m | 77.8 |
| A5β | 77.4, CH | 3.60, m | 77.4, CH | 3.60, m | 77.4, CH | 3.60, m | 75.6 |
| A6β | 63.5, CH2 | 3.91, m | 63.5, CH2 | 3.91, m | 63.5, CH2 | 3.91, m | 61.5 |
| B1 | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) | 100.7 |
| B2 | 74.4, CH | 3.63, m | 74.4, CH | 3.63, m | 74.4, CH | 3.63, m | 72.6 |
| B3 | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m | 74.4 |
| B4 | 79.8, CH | 3.67, m | 79.9, CH | 3.67, m | 79.8, CH | 3.67, m | 78.0 |
| B5 | 74.0, CH | 3.85, m | 74.0, CH | 3.85, m | 74.0, CH | 3.85, m | 72.2 |
| B6 | 63.4, CH2 | 3.84, m | 63.2, CH2 | 3.84, m | 63.4, CH2 | 3.84, m | 61.5 |
| C1 | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) | 100.7 |
| C2 | 74.4, CH | 3.63, m | 74.4, CH | 3.63, m | 74.4, CH | 3.63, m | 72.6 |
| C3 | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m | 74.4 |
| C4 | 79.8, CH | 3.67, m | 79.9, CH | 3.67, m | 79.8, CH | 3.67, m | 78.0 |
| C5 | 74.0, CH | 3.85, m | 74.0, CH | 3.85, m | 74.0, CH | 3.85, m | 72.2 |
| C6 | 63.5, CH2 | 3.84, m | 63.2, CH2 | 3.84, m | 63.4, CH2 | 3.84, m | 61.5 |
| D1 | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) | 102.5, CH | 5.41, d (3.5) | 100.7 |
| D2 | 74.4, CH | 3.67, m | 74.4, CH | 3.67, m | 74.4, CH | 3.66, m | 72.6 |
| D3 | 76.2, CH | 3.95, m | 76.2, CH | 3.96, m | 76.2, CH | 3.96, m | 74.4 |
| D4 | 80.7, CH | 3.67, m | 80.7, CH | 3.67, m | 80.8, CH | 3.66, m | 78.0 |
| D5 | 71.7, CH | 4.05, m | 71.8, CH | 4.05, m | 71.8, CH | 4.06, m | 72.2 |
| D6a | 66.5, CH2 | 4.43, dd (12.5, 2.0) | 66.3, CH2 | 4.44, dd (12.5, 2.0) | 66.5, CH2 | 4.50, dd (12.5, 2.0) | 61.5 |
| D6b | 4.24, brd (12.5) | 4.24, brd (12.5) | 4.26, brd (12.5) | ||||
| E1 | 103.4, CH | 5.30, d (3.5) | 103.4, CH | 5.29, d (3.5) | 103.4, CH | 5.28, d (3.5) | 101.0 |
| E2 | 74.4, CH | 3.59, m | 74.2, CH | 3.58, m | 74.2, CH | 3.59, m | 70.7 |
| E3 | 75.47, CH | 3.62, m | 75.6, CH | 3.62, m | 75.6, CH | 3.62, m | 73.8 |
| E4 | 67.7, CH | 2.48, t (9.0) | 67.9, CH | 2.46, t (9.0) | 67.9, CH | 2.47, t (9.0) | 66.0 |
| E5 | 72.4, CH | 3.72, m | 72.7, CH | 3.71, m | 72.6, CH | 3.73, m | 70.7 |
| E6 | 20.2, CH3 | 1.32, d (6.0) | 20.2, CH3 | 1.31, d (6.0) | 20.2, CH3 | 1.32, d (6.0) | 18.4 |
| F1 | 58.8, CH | 3.54, m | 58.8, CH | 3.53, m | 58.9, CH | 3.54, m | 57.1 |
| F2 | 75.52, CH | 3.66, m | 75.7, CH | 3.66, m | 75.7, CH | 3.66, m | 74.0 |
| F3 | 75.8, CH | 3.76, m | 75.8, CH | 3.77, m | 75.8, CH | 3.76, m | 73.8 |
| F4 | 73.5, CH | 4.05, d (6.4) | 73.7, CH | 4.05, d (6.4) | 73.9, CH | 4.04, d (6.4) | 72.2 |
| F5 | 142.3, C | 141.9, C | 141.9, C | 140.1 | |||
| F6a | 64.4, CH2 | 4.23, brd (13.6) | 64.4, CH2 | 4.24, brd (13.6) | 64.4, CH2 | 4.23, brd (13.6) | 62.6 |
| F6b | 4.12, brd (13.6) | 4.12, brd (13.6) | 4.12, brd (13.6) | ||||
| F7 | 126.1, CH | 5.90, dd (5.0, 1.0) | 126.6, CH | 5.91, dd (5.0, 1.0) | 126.5, CH | 5.90, dd (5.0, 1.0) | 124.8 |
| D6-O-acetyl | 177.0, C | - | - | - | - | - | |
| 23.1, CH3 | 2.16, s | - | - | - | - | - | |
| D6-O-propionyl | - | - | 180.3, C | - | - | - | |
| - | - | 30.0, CH2 | 2.48, q (7.5) | - | - | - | |
| - | - | 11.1, CH3 | 1.13, t (7.5) | - | - | - | |
| D6-O-2-hydroxy-butyryl | - | - | - | - | 176.6, C | - | |
| - | - | - | - | 45.9, CH2 | 2.67, dd (15.0, 4.5) 2.59, dd (15.0, 8.0) |
- | |
| - | - | - | - | 67.3, CH2 | 4.28, m | - | |
| - | - | - | - | 24.8, CH3 | 1.26, d (6.0) | - | |
a Measured at 500 MHz for 1H and 125 MHz for 13C NMR, 298 K, 6.0 mg/mL for 3 and 20.0 mg/mL for 4; b Measured at 400 MHz for 1H and 100 MHz for 13C NMR, 298 K, 4.0 mg/mL for 5; c unstable in D2O.