Table 1.
The NMR spectroscopic data (δ) of compounds 1 and 2a.
| No. |
1b |
2 |
||
|---|---|---|---|---|
| δH | δC | δH | δC | |
| 2 | 126.9 | 85.6 | ||
| 3 | 134.5 | 200.0 | ||
| 3a | 122.3 | 122.0 | ||
| 4 | 7.63 brd (8.4) | 118.5 | 7.25 brd (7.2) | 125.0 |
| 5 | 6.90 dt (1.2, 8.4) | 119.8 | 6.52 brt (7.2) | 118.8 |
| 6 | 6.97 dt (1.2, 8.4) | 122.2 | 7.23 dt (1.2, 7.2) | 138.3 |
| 7 | 7.22 brd (8.4) | 112.4 | 6.74 brd (7.2) | 113.1 |
| 7a | 134.8 | 163.6 | ||
| 8a | 6.25 s | 54.9 | 3.99 d (15.0) | 29.3 |
| 8b | 3.56 d (15.0) | |||
| 2ʹ | 7.54 s | 125.3 | 6.96 s | 125.0 |
| 3ʹ | 112.3 | 108.9 | ||
| 3ʹa | 128.7 | 129.4 | ||
| 4ʹ | 7.73 brd (8.4) | 120.4 | 7.66 brd (7.2) | 119.9 |
| 5ʹ | 6.92 dt (1.2, 8.4) | 119.8 | 6.94 dt (1.2, 7.2) | 119.6 |
| 6ʹ | 7.00 dt (1.2, 8.4) | 122.2 | 6.97 dt (1.2, 7.2) | 122.0 |
| 7ʹ | 7.27 brd (8.4) | 122.6 | 7.16 brd (7.2) | 111.9 |
| 7ʹa | 137.3 | 137.4 | ||
a
1H and 13C NMR data (δ) were measured at 600 and 150 MHz in CD3OD for 1 and 2, respectively. Proton coupling constants (J) in Hz are given in parentheses. The assignments were based on 1H—1H COSY, HSQC, and HMBC experiments.
b
Data for glucopyranosyl in 1: δH 4.70 (1 H, d, J = 7.8 Hz, H-1ʺ), 3.53 (1 H, dd, J = 7.8, 9.0 Hz, H-2ʺ), 3.40 (1 H, t, J = 9.0 Hz, H-3ʺ), 3.31 (1 H, t, J = 9.0 Hz, H-4ʺ), 3.18 (1 H, m, H-5ʺ), 3.82 (1 H, dd, J = 12.0, 2.4 Hz, H-6ʺa), 3.71 (1 H, dd, J = 12.0, 6.6 Hz, H-6″b); δC 106.7 (C-1ʺ), 75.5 (C-2ʺ), 78.0 (C-3ʺ), 71.9 (C-4ʺ), 78.8 (C-5ʺ), 63.2 (C-6ʺ).