Table 1. 1H NMR (600 MHz) and 13C NMR (150 MHz) spectroscopic data of compounds 1–3 in CDCl3 (δ in ppm, J in Hz).
Position | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δ C (type) | δ H (mult., J in Hz) | δ C (type) | δ H (mult., J in Hz) | δ C (type) | δ H (mult., J in Hz) | |
1 | 65.5 (CH) | 3.74 (m) | 68.1 (CH) | 5.19 (t, 4.8) | 79.1 (CH) | 4.62 (dd, 11.4, 5.9) |
2a | 26.7 (CH2) | 1.64 (m) | 41.3 (CH2) | 1.46 (m) | 23.5 (CH2) | 1.88 (m) |
2b | 1.25 (m) | 1.13 (m) | 1.78 (d, 12.5) | |||
3a | 33.4(CH2) | 1.78 (d, 10.3) | 28.2(CH2) | 2.20 (m) | 36.7 (CH2) | 1.50 (m) |
3b | 1.28 (m) | 1.91 (dd, 16.7, 5.0) | 1.54 (d, 5.3) | |||
4 | 33.7 (C) | 33.9 (C) | 31.1 (C) | |||
5 | 51.3 (CH) | 1.86 (d, 4.2) | 59.8 (CH) | 1.21 (d, 7.0) | 54.6 (CH) | 2.97 (s) |
6 | 75.2 (CH) | 5.20 (d, 4.2) | 74.5 (CH) | 3.78 (dd, 11.9, 7.0) | 102.1 (CH) | 5.34 (s) |
7 | 97.2 (C) | 94.7 (C) | 173.1 (C) | |||
8 | 51.6 (C) | 59.3 (C) | 54.3 (C) | |||
9 | 39.8 (CH) | 2.89 (d, 2.4) | 52.9 (CH) | 1.54 (m) | 51.2 (CH) | 3.79 (s) |
10 | 41.7 (C) | 36.8 (C) | 47.7 (C) | |||
11a | 123.3 (CH) | 5.76 (dd, 9.4, 2.4) | 18.3 (CH) | 1.44 (m) | 210.3 (C) | |
11b | 1.36 (m) | |||||
12a | 138.6 (CH) | 6.36 (t, 8.2) | 30.5 (CH2) | 1.34 (m) | 52.5 (CH2) | 2.68 (dd, 16.0, 7.9) |
12b | 1.18 (m) | 2.46 (d, 16.0) | ||||
13 | 38.6 (CH) | 2.97 (dd, 7.4, 4.5) | 28.6 (CH) | 3.44 (m) | 36.8 (CH) | 3.07 (m) |
14a | 31.8 (CH2) | 1.95 (dd, 11.6, 4.5) | 28.4 (CH2) | 2.73 (m) | 36.5 (CH2) | 1.96 (dd, 12.4, 4.1) |
14b | 1.55 (d, 11.6) | 1.95 (dd, 16.5, 9.5) | 1.74 (d, 12.4) | |||
15 | 74.3 (CH) | 4.60 (s) | 221.7 (C) | 79.4 (CH) | 5.24 (s) | |
16 | 155.6 (C) | 56.3 (CH) | 2.74 (m) | 153.9 (C) | ||
17a | 107.5 (CH2) | 5.05 (s) | 66.4 (CH2) | 4.08 (d, 9.2) | 111.5 (CH2) | 5.41 (s) |
17b | 5.00 (d, 2.4) | 5.37 (s) | ||||
18 | 31.7 (CH3) | 1.13 (s) | 33.7 (CH3) | 1.12 (s) | 32.9 (CH3) | 1.08 (s) |
19 | 21.6 (CH3) | 0.89 (s) | 22.4 (CH3) | 1.10 (s) | 23.7 (CH3) | 0.97 (s) |
20a | 66.4 (CH2) | 3.81 (dd, 9.0, 2.5) | 68.8 (CH2) | 4.17 (d, 9.5) | 72.1 (CH2) | 4.04 (d, 9.2) |
20b | 3.79 (d, 9.0) | 3.70 (dd, 9.5, 3.0) | 3.93 (d, 9.2) | |||
OAc-6 | 170.9 | |||||
21.4 (CH3) | 2.18 (s) | |||||
OAc-1 | 169.8 (C) | |||||
21.9 (CH3) | 2.10 (s) | |||||
OEt–CH2 | 66.7 (CH2) | 3.49 (m) | ||||
OEt–CH3 | 15.1 (CH3) | 1.17 (t, 7.0) |