Table 2. 1H and 13C NMR Data for Sugar Moieties of Compounds 1–3a.
|
1 |
2 |
3 |
||||
|---|---|---|---|---|---|---|
| position | δH | δC | δH | δC | δH | δC |
| ara-1 at C-3 | 4.44, d (6.8) | 105.7 | 4.44, d (6.7) | 105.8 | 4.44, d (6.8) | 106.0 |
| 2 | 3.91, dd (9.0, 6.8) | 75.0 | 3.93, dd (9.0, 6.7) | 75.0 | 3.93, dd (9.0, 6.8) | 75.1 |
| 3 | 3.95, dd (9.0, 2.0) | 83.0 | 3.91, dd (9.0, 3.0) | 82.7 | 3.91, dd (9.0, 2.5) | 82.3 |
| 4 | 4.08, m | 70.0 | 4.08, m | 70.0 | 4.07, m | 71.0 |
| 5a | 3.88, dd (12.0, 2.0) | 66.2 | 3.87, dd (12.0, 2.5) | 66.0 | 3.90, dd (12.0, 2.0) | 66.5 |
| 5b | 3.65, dd (12.0, 4.0) | 3.61, dd (12.0, 4.0) | 3.62, dd (12.0, 4.5) | |||
| glc I-1 | 4.68, d (7.7) | 103.0 | 4.66, d (7.5) | 102.8 | 4.68, d (8.0) | 102.9 |
| 2 | 3.66b | 77.0 | 3.64b | 77.8 | 3.60, dd (9.5, 8.0) | 77.8 |
| 3 | 3.65b | 83.4 | 3.65b | 83.3 | 3.66, t (9.5) | 83.6 |
| 4 | 3.28, t (9.5) | 71.0 | 3.40, t (9.5) | 70.6 | 3.39, t (9.5) | 71.0 |
| 5 | 3.55, m | 76.7 | 3.33, m | 77.9 | 3.31, m | 78.0 |
| 6a | 4.20, dd (12.0, 3.0) | 70.0 | 3.88, dd (12.0, 3.5) | 62.0 | 3.88, dd (12.0, 3.0) | 62.4 |
| 6b | 3.72, dd (12.0, 5.0) | 3.72, dd (12.0, 5.0) | 3.72, dd (12.0, 4.5) | |||
| rha-1 | 5.61, d (1.8) | 101.0 | 5.62, d (1.5) | 100.7 | 5.64, d (1.8) | 100.0 |
| 2 | 3.95, dd (3.0, 1.8) | 72.0 | 3.96, dd (3.0, 1.5) | 72.0 | 3.96, dd (3.0, 1.8) | 72.1 |
| 3 | 3.73, dd (9.0, 3.0) | 72.0 | 3.74, dd (9.0, 3.0) | 71.8 | 3.72, dd (9.0, 3.0) | 72.0 |
| 4 | 3.45, t (9.0) | 74.0 | 3.45, t (9.0) | 73.5 | 3.47, t (9.0) | 73.0 |
| 5 | 4.07, m | 70.0 | 4.10, m | 70.0 | 4.09, m | 70.5 |
| 6 | 1.26, d (6.5) | 17.0 | 1.25, d (6.8) | 17.4 | 1.28, d (6.5) | 18.0 |
| glc II-1 | 4.77, d (7.5) | 105.7 | 4.78, d (7.5) | 105.3 | 4.79, d (7.5) | 105.6 |
| 2 | 3.38, dd (9.5, 7.5) | 75.0 | 3.40b | 75.0 | 3.39, dd (9.0, 7.5) | 75.6 |
| 3 | 3.34, t (9.5) | 78.0 | 3.42, t (9.0) | 78.0 | 3.44, t (9.0) | 78.0 |
| 4 | 3.40, t (9.5) | 70.0 | 3.40b | 71.0 | 3.43, t (9.0) | 71.0 |
| 5 | 3.36, m | 77.0 | 3.33, m | 77.9 | 3.31, m | 78.3 |
| 6a | 3.93, dd (12.0, 3.0) | 62.0 | 3.90, dd (12.0, 2.5) | 62.1 | 3.93, dd (12.0, 3.0) | 62.1 |
| 6b | 3.75, dd (12.0, 4.5) | 3.80, dd (12.0, 4.5) | 3.77, dd (12.0, 5.0) | |||
| glc III-1 | 4.33, d (7.4) | 104.9 | ||||
| 2 | 3.23, dd (9.0, 7.4) | 75.0 | ||||
| 3 | 3.35, t (9.0) | 77.0 | ||||
| 4 | 3.28, t (9.0) | 71.0 | ||||
| 5 | 3.41, m | 77.0 | ||||
| 6a | 3.90, dd (12.0, 3.0) | 62.0 | ||||
| 6b | 3.69, dd (12.0, 5.0) | |||||
| glc-1 at C-28 | 5.45, d (8.0) | 95.9 | 5.46, d (8.0) | 95.7 | ||
| 2 | 3.29, dd (9.5, 8.0) | 75.0 | 3.35, dd (9.5, 8.0) | 73.4 | ||
| 3 | 3.41b | 77.7 | 3.33, t (9.5) | 77.9 | ||
| 4 | 3.40b | 70.0 | 3.40b | 70.6 | ||
| 5 | 3.36, m | 77.0 | 3.40b | 78.0 | ||
| 6a | 3.83, dd (12.0, 3.0) | 62.0 | 3.86, dd (12.0, 2.5) | 62.0 | ||
| 6b | 3.70, dd (12.0, 4.5) | 3.72, dd (12.0, 5.0) | ||||
| rha-1 at C-28 | 6.00, d (1.8) | 95.5 | ||||
| 2 | 3.96, dd (3.0, 1.8) | 72.1 | ||||
| 3 | 3.72, dd (9.5, 3.0) | 72.0 | ||||
| 4 | 3.44, t (9.5) | 73.0 | ||||
| 5 | 4.09, m | 70.5 | ||||
| 6 | 1.24, d (6.0) | 18.0 | ||||
a
Spectra were recorded in methanol-d4 at 600 MHz (1H) and 150 MHz (13C). J values are in parentheses and reported in Hz; chemical shifts are given in ppm; assignments were confirmed by COSY, 1D-TOCSY, HSQC, and HMBC experiments.
b
Overlapped signal.