Table 3.
1H and 13C NMR Data for Compounds 13 - 15 in CD3OD at 600 and 150 MHz, respectively.
cmpd. | 13 | 14 | 15a | |||
---|---|---|---|---|---|---|
pos# | δC, typeb | δH (J[Hz]) | δC, typeb | δH (J[Hz]) | δ C, typeb | δH (J[Hz]) |
1 | 172.5, C | 169.5, C | 167.7, C | |||
2 | 41.9, CH2 | 2.73, dd (15.2, 4.2) | 101.8, CH | 5.22, s | 46.8, CH2 | 3.90, d (14.8) |
2.67, dd (15.2, 8.0) | 3.78, d (14.8) | |||||
3 | 50.7, CH | 5.21, dd (8.0, 4.2) | 155.1, C | 191.6, C | ||
4 | 171.2, C | 170.6, C | 172.1, C | |||
5 | 57.0, CH | 5.71, dd (9.8, 6.4) | 57.9, CH | 6.07, dd (11.4, 4.8) | 56.4, CH | 5.74, dd (11.2, 4.8) |
6 | 175.2, C | 175.6, C | 174.2, C | |||
7 | 47.2, CH | 4.68, m | 47.3, CH | 4.77, m | 45.7, CH | 4.40, q (6.6) |
8 | 177.9, C | 177.8, C | 177.3, C | |||
9 | 40.4, CH | 2.65, m | 38.7, CH | 2.71, dqd (11.8, 7.2, 1.2) | 39.7, CH | 2.33, m |
10 | 42.6, CH2 | 2.21, dd (15.2, 11.4) | 41.3, CH2 | 2.35, dd (17.0, 11.8) | 43.5, CH2 | 2.19, dd (13.8, 9.2) |
1.93, d (15.2) | 1.85, d (17.0) | 1.82, dd (13.8, 4.8) | ||||
11 | 134.1, C | 134.7, C | 131.4, C | |||
12 | 130.4, CH | 4.83c | 127.7, CH | 4.80c | 132.5, CH | 4.74, d (8.8) |
13 | 30.6, CH | 2.30, m | 30.7, CH | 2.41, m | 28.9, CH | 2.03, m |
14 | 44.2, CH2 | 1.50, m | 44.8, CH2 | 1.55, ddd (12.2, 12.0, 4.0) | 43.2, CH2 | 1.39, ddd (13.8, 9.0, 6.6) |
1.18, m | 1.33, ddd (12.0, 10.8, 3.6) | 1.20, ddd (13.8, 7.8, 4.2) | ||||
15 | 71.8, CH | 4.68, m | 70.7, CH | 4.81, m | 71.3, CH | 4.85, dqd (9.0, 6.2, 4.2) |
16 | 133.6, C | 127.8, C | 129.3, C | |||
17 | 118.5, CH | 6.49, dd (8.2, 2.0) | 121.1, CH | 6.86, dd (8.2, 2.0) | 123.4, CH | 7.41, d (8.2, 1.2) |
17′ | 114.5, CH | 6.70, d (2.0) | 116.0, CH | 6.91, d (2.0) | 115.0, C | |
18 | 116.5, CH | 6.67, d (8.2) | 116.0, CH | 6.79, d (8.2) | 115.3, CH | 7.52, d (1.2) |
18′ | 146.5, C | 146.1, C | 144.5, C | |||
19 | 145.8, C | 149.0, C | 150.4, CH | 6.84, d (8.2) | ||
20 | 25.1, CH2 | 3.22, m | 24.0, CH2 | 3.26, dd (15.4, 4.8) | 23.5, CH2 | 3.48, dd (15.4, 4.8) |
3.18, dd (15.4, 11.6) | 3.17, dd (15.4, 11.2) | |||||
21 | 110.3, C | 110.3, C | 110.8, C | |||
22 | 128.7, C | 128.9, C | 127.6, C | |||
23 | 119.3, CH | 7.54, d (8.0) | 119.2, CH | 7.55, dt (8.0, 0.6) | 118.3, CH | 7.53, d (8.0) |
24 | 120.6, CH | 7.00, td (8.0, 1.0) | 120.6, CH | 7.03, td (8.0, 0.8) | 120.5, CH | 7.09, td (8.0, 0.8) |
25 | 123.0, CH | 7.07, td (8.0, 1.0) | 123.0, CH | 7.09, td (8.0, 0.8) | 122.7, CH | 7.14, td (8.0, 0.8) |
26 | 111.8, CH | 7.25, d (8.0) | 111.7, CH | 7.25, dt (8.0, 0.6) | 110.7, CH | 7.25c |
27 | 138.1, C | 138.1, C | 136.2, C | |||
28 | 110.6, C | 110.5, C | 109.1, C | |||
29 | 18.1, CH3 | 0.66, d (6.6) | 17.9, CH3 | 0.49, d (6.6) | 16.2, CH3 | 0.72, d (6.6) |
30 | 20.2, CH3 | 1.08, d (6.8) | 21.3, CH3 | 1.06, d (7.2) | 18.4, CH3 | 1.04, d (6.8) |
31 | 18.5, CH3 | 1.59, d (0.8) | 18.9, CH3 | 1.62, s | 16.2, CH3 | 1.29, s |
32 | 22.2, CH3 | 0.85, d (6.6) | 22.7, CH3 | 0.87, d (6.6) | 20.5, CH3 | 0.72, d (6.6) |
33 | 19.7, CH3 | 1.07, d (6.2) | 19.3, CH3 | 1.14, d (6.2) | 20.6, CH3 | 1.15, d (6.2) |
34 | 31.8, CH3 | 3.08, s | 32.1, CH3 | 2.98, s | 32.1, CH3 | 3.10, s |
Spectra recorded in CDCl3
Carbon type determined from gHMQC data
Shift assigned based on gHMQC and gHMBC data