Table 2.
1H and 13C NMR Spectroscopic Data of 1–3 (δ in ppm, J in Hz)
| Position | 1 | 2 | 3 | |||
|---|---|---|---|---|---|---|
| δ aH | δ cC | δ aH | δ dC | δ bH | δ dC | |
| 2 | 131.9 | 131.0 | 130.3 | |||
| 3 | 4.20 (dd, 3.7, 11.7) | 57.7 | 4.29 (d, 12.2) | 75.0 | 4.59 (br. s) | 71.6 |
| 5 | 3.34 (dd, 5.1, 12.0) | 51.1 | 3.76 (overlap) | 63.2 | 3.66 (overlap) | 69.4 |
| 3.16 (ddd, 5.1, 7.4, 12.0) | 3.56 (m) | 3.66 (overlap) | ||||
| 6 | 2.99 (m) | 20.6 | 3.29 (overlap) | 18.9 | 3.09 (m) | 20.6 |
| 2.88 (dt, 5.1, 5.1, 10.9) | 2.88 (br. d, 14.1) | 3.02 (m) | ||||
| 7 | 107.5 | 106.9 | 106.8 | |||
| 8 | 127.5 | 127.9 | 127.6 | |||
| 9 | 7.41 (d, 7.8) | 119.0 | 7.46 (d, 7.8) | 119.6 | 7.36 (d, 7.8) | 119.1 |
| 10 | 7.00 (t, 7.8) | 120.3 | 7.00 (t, 7.8) | 120.7 | 6.96 (t, 7.8) | 120.7 |
| 11 | 7.09 (t, 7.8) | 123.0 | 7.08 (t, 7.8) | 123.3 | 7.05 (t, 7.8) | 123.4 |
| 12 | 7.30 (d, 7.8) | 112.2 | 7.28 (d, 7.8) | 112.5 | 7.28 (d, 7.8) | 112.6 |
| 13 | 138.5 | 138.9 | 138.9 | |||
| H α -14 | 2.42 (ddd, 3.7, 7.9, 14.0) | 32.6 | 2.23 (m) | 34.6 | 2.26 (ddd, 2.2, 12.8, 14.2) | 25.1 |
| H β -14 | 2.30 (ddd, 8.9, 11.7, 14.0) | 2.34 (m) | 2.60 (dt, 5.0, 14.2) | |||
| 15 | 4.09 (d, 7.9) | 33.6 | 4.10 (d, 6.9) | 36.2 | 1.47 (tt, 1.5, 12.2, 12.8) | 35.1 |
| 16 | 117.5 | 117.7 | 2.78 (ddd,2.8, 6.1, 8.5) | 49.1 | ||
| 17 | 7.20 (s) | 158.5 | 7.16 (s) | 158.1 | 3.92 (dd, 8.4, 11.0) | 62.3 |
| 3.52 (dd, 6.3, 11.0) | ||||||
| 18 | 1.64 (d, 6.6) | 13.5 | 1.68 (d, 6.4) | 14.3 | 5.18 (dd, 1.8, 17.1) | 120.4 |
| 5.08 (dd, 1.8, 10.0) | ||||||
| 19 | 5.53 (q, 6.6) | 126.5 | 5.73 (q, 6.4) | 131.4 | 5.31 (m) | 137.4 |
| 20 | 133.0 | 132.8 | 3.04 (m) | 40.7 | ||
| H α -21 | 3.62 (d, 13.1) | 61.1 | 5.07 (d, 11.7) | 78.7 | 3.32 (t, 11.9) | 63.0 |
| H β -21 | 4.07 (d, 13.1) | 3.76 (overlap) | 2.90 (dd, 3.5, 11.9) | |||
| 22 | 174.7 | 175.5 | 174.4 | |||
| OMe - 17 | 3.74 (s) | 61.4 | 3.72 (s) | 61.6 | ||
| OMe - 22 | 3.64 (s) | 52.0 | ||||
aRecorded at 400 MHz in CD3OD
bRecorded at 600 MHz in CD3OD
cRecorded at 100 MHz in CD3OD
dRecorded at 150 MHz in CD3OD