Table 1.
1H-NMR data of compounds 1–6 [MeOH-d4, 500 MHz, δ ppm (J = Hz)].
1 | 2 | 3 | 4 | 5 | 6 | |
---|---|---|---|---|---|---|
1 | 3.56 ddd (9.6, 7.1, 7.1) | 3.60 m | 3.47 ddd (9.5, 7.8, 7.2) | 3.01 dd (9.7, 7.2, 7.2) | 3.01 ddd (9.4, 7.1, 7.1) | 2.96 ddd (9.3, 7.3, 7.3) |
2a | 2.45 ddd (14.7, 7.1, 5.3) | 2.49 ddd (14.6, 7.0, 5.5) | 2.40 m | 2.10 ddd (13.1, 7.2, 7.0) | 2.09 ddd (13.4, 7.1, 7.1) | 2.10 ddd (13.8, 7.3, 7.1) |
2b | 1.51 ddd (14.7, 10.0, 7.1) | 1.54 dd (14.6, 10.2, 7.0) | 1.60 ddd (14.0, 10.1, 7.8) | 1.75 ddd (13.1, 9.3, 7.2) | 1.74 ddd (13.4, 9.3, 7.1) | 1.71 ddd (13.8, 9.4, 7.3) |
3 | 4.07 m | 4.10 m | 4.07 m | 4.51 t (9.3, 7.0) | 4.51 dd (9.3, 7.1) | 4.48 dd (9.4, 7.1) |
5 | 2.26 t (9.6) | 2.28 dd (9.8, 9.2) | 2.28 dd (10.2, 9.7) | 2.90 t (10.1, 9.7) | 2.91 dd (10.2, 9.4) | 2.84 m |
6 | 4.86 dd (9.6, 9.2) | 4.91 dd (9.8, 9.2) | 4.80 m | 4.34 t (10.1) | 4.35 t (10.2) | 4.16 dd (10.3, 9.2) |
7 | 3.15 br t (9.2) | 3.17 m | 3.20 m | 3.26 m | 3.28 m | 2.87 m |
8 | 5.12 m | 5.12 m | 5.12 m | 5.12 m | 5.15 m | 3.87 ddd (9.3, 4.8, 4.3) |
9a | 2.67dd (15.0, 4.5) | 2.71 dd (15.0, 4.8) | 2.75 dd (14.5, 5.0) | 2.73 dd (14.5, 4.9) | 2.73 dd (14.5, 5.0) | 2.67 dd (13.8, 4.8) |
9b | 2.38 br d (15.0) | 2.42 br d (15.0) | 2.38 dd (14.5, 3.2) | 2.38 br d (14.5) | 2.40 dd (14.5, 2.9) | 2.25 dd (13.8, 4.3) |
13a | 6.07 d (2.8) | 6.10 d (3.3) | 6.11 d (3.0) | 6.18 d (2.5) | 6.13 d (3.1) | 6.16 d (3.2) |
13b | 5.59 d (2.8) | 5.57 d (3.3) | 5.45 d (3.0) | 5.59 d (2.5) | 5.65 d (3.1) | 6.14 d (3.2) |
14a | 5.08 br s | 5.10 br s | 5.12 br s | 5.15 br s | 5.17 br s | 5.09 br s |
14b | 4.75 br s | 4.77 br s | 4.85 br s | 4.91 br s | 4.92 br s | 4.97 br s |
15a | 4.14 d (11.7) | 4.19 d (11.7) | 4.02 d (11.8) | 5.44 br s | 5.44 br s | 5.40 br s |
15b | 3.80 d (11.7) | 3.83 d (11.7) | 3.81 d (11.8) | 5.34 br s | 5.34 br s | 5.31 br s |
3′a | 6.28 br s | 6.18 br s | 6.31 br s | 6.13 d (2.5) | 6.31 br s | - |
3′b | 5.94 br s | 5.73 br s | 5.97 br s | 5.73 d (2.5) | 5.97 br s | - |
4′ | 4.28 s (2H) | 1.98 s | 4.31 s (2H) | 1.97 s | 4.31s (2H) | - |