Table 1.
NMR spectral data for DHPA, ThA, and ThBa
| Position | NMR spectral data |
|||||
|---|---|---|---|---|---|---|
| DHPA |
ThA |
ThB |
||||
|
1H (ppm) |
13C (ppm) |
1H (ppm) |
13C (ppm) |
1H (ppm) |
13C (ppm)b | |
| 1 | 162.5 | 1.38, s, 3H | 26.2 | 1.36, s, 3H | 26.3 | |
| 1-OH | 13.07, s | |||||
| 2 | 7.28, dd, 1.2, 8.4 | 124.8 | 73.8 | |||
| 2-OH | Exchange | Exchange | ||||
| 3 | 7.59, dd, 7.5, 8.5 | 135.6 | 3.18, dd, 16.5, 1.5 (A) | 40.9 | 3.23, d, 16.7 (A) | 41.5 |
| 3.00, d, 16.5 (B) | 3.06, d, 16.7 (B) | |||||
| 3a | 133.7 | |||||
| 4 | 7.75, dd, 1.2, 7.5 | 118.8 | 6.99, d, 1.5 | 118.3 | 7.42, s | 113.2 |
| 4a | 132.8 | 139.4 | ||||
| 5 | 7.65, d, 2.6 | 112.6 | 7.13, dd, 0.9, 8.2 | 118.0 | ||
| 5-OH | 9.16, s, brd | |||||
| 6 | 150.9 | 7.46, dd, 7.7, 8.3 | 132.4 | 6.98, d, 8.4 | 115.4 | |
| 6-OH | 5.81, s, brb | |||||
| 7 | 7.02, d, 2.6 | 124.1 | 6.83, dd, 0.9, 7.7 | 110.8 | 6.61, d, 8.4 | 110.1 |
| 8 | 140.2 | 158.0 | ||||
| 8-OH | 9.72, d, 1.0 | 8.65, s, brd | ||||
| 8a | 124.2 | 112.9 | ||||
| 9 | 189.7 | 165.3 | ||||
| 9-OH | 15.92, d, 1.0 | Exchange | ||||
| 9a | 117.0 | 108.6 | ||||
| 10 | 183.0 | 206.6 | ||||
| 10a | 137.9 | |||||
| 11 | 3.20, m, 2H | 38.1 | 2.50, ddd, 10.2, 3.6, 1.0 | 60.7 | 2.53, m | 61.4 |
| 12 | 1.69, m, 2H | 23.9 | 1.80, m, (A) | 21.6 | 1.90, m | 21.6 |
| 1.59, m, (B) | 1.58, m | |||||
| 13 | 1.05, t, 3H | 14.3 | 1.11, t, 3H | 13.1 | 1.06, t, 3H | 13.2 |
a
Chemical shifts are reported relative to tetramethyl silane, which was used as an internal standard. Measurements were conducted in CDCl3 (DHPA) and acetone-d6.
b
Values were obtained indirectly via heteronuclear single quantum coherence spectroscopy measurements.