Table 1.
1H (400 MHz) and 13C (100 MHz) NMR data for 1–4 in CDCl3
No. | 1 |
2 |
3 |
4 |
||||
---|---|---|---|---|---|---|---|---|
δ C | δH (J in Hz) | δ C | δH (J in Hz) | δ C | δH (J in Hz) | δ C | δH (J in Hz) | |
1 | 53.3 d | 1.49 m | 51.3 d | 2.25 m | 51.5 d | 2.23 m | 135.5 d | 5.14 dd (11.4, 4.0) |
2 | 74.1 d | 4.83 t (8.0) | 75.1 d | 5.20 t (3.9) | 75.2 d | 5.23 t (3.6) | 25.9 t | 2.25 m; 2.25 m |
3 | 38.6 t | 1.89 m; 1.70 m | 48.1 t | 1.95 m; 1.88 m | 48.0 t | 1.92 m; 1.90 m | 39.6 t | 2.35 m; 2.15 m |
4 | 80.6 d | 3.49 t (8.7) | 78.7 s | 78.8 s | 143.3 s | |||
5 | 44.9 s | 51.9 d | 1.72 m | 52.0 d | 1.70 m | 128.0 d | 4.86 d (9.3) | |
6 | 37.0 t | 1.41 dd (14.8, 5.1); 1.10 m | 28.1 t | 1.88 m; 1.17 m | 28.5 t | 1.85 m; 1.12 m | 72.9 d | 5.08 dd (9.3, 7.3) |
7 | 48.4 d | 2.85 m | 50.9 d | 2.40 t (10.0) | 50.0 d | 2.47 t (10.5) | 51.5 d | 2.65 m |
8 | 83.0 d | 4.28 m | 80.1 d | 4.43 dd (10.0, 2.0) | 83.7 d | 4.56 dd (10.5, 2.0) | 68.9 d | 4.63 d (2.9) |
9 | 44.8 t | 2.39 m; 1.27 m | 128.0 d | 5.79 d (2.0) | 127.1 d | 5.83 d (2.0) | 45.8 t | 2.83 m; 2.42 dd (14.1, 1.7) |
10 | 28.6 d | 1.89 m | 135.3 s | 136.2 s | 134.3 s | |||
11 | 58.1 s | 55.9 s | 57.9 s | 55.9 s | ||||
12 | 184.8 s | 176.5 s | 184.7 s | 182.4 s | ||||
13 | 33.1 t | 2.22 dd (12.6, 3.3); 2.04 m | 31.1 t | 2.18 m; 2.00 m | 32.5 t | 2.22 m; 2.00 m | 34.7 t | 2.35 m; 1.72 m |
14 | 19.6 q | 0.94 d (6.6) | 22.6 q | 1.76 s | 22.6 q | 1.79 s | 60.6 t | 4.25 d (11.5); 3.87 d (11.5) |
15 | 18.8 q | 0.84 s | 25.1 q | 1.10 s | 25.1 q | 1.10 s | 17.5 q | 1.68 d (0.8) |
1′ | 69.5 s | 67.8 s | 69.3 s | 72.3 s | ||||
2′ | 85.6 d | 3.42 d (9.8) | 82.4 d | 4.54 s | 85.5 d | 3.45 d (9.1) | 83.6 d | 4.47 s |
3′ | 52.6 d | 2.62 br s | 48.1 d | 2.69 s | 52.2 d | 2.62 br s | 48.9 d | 2.73 m |
4′ | 140.1 s | 138.7 s | 139.7 s | 139.3 s | ||||
5′ | 133.9 s | 134.8 s | 134.4 s | 132.8 s | ||||
6′ | 25.5 t | 2.85 m; 2.22 dd (12.6, 3.3) | 25.7 t | 3.03 dd (16.4, 1.8); 2.18 m | 25.8 t | 2.96 br d (16.6); 2.15 m | 26.2 t | 3.04 dd (16.2, 2.6); 1.95 m |
7′ | 45.1 d | 2.85 m | 44.6 d | 2.64 m | 44.5 d | 2.64 m | 45.5 d | 2.60 m |
8′ | 81.0 d | 4.28 m | 81.6 d | 4.26 ddd (13.4, 12.1, 3.3) | 81.5 d | 4.27 ddd (13.0, 12.0, 3.4) | 81.0 d | 4.06 ddd (12.0, 9.0, 2.6) |
9′ | 36.7 t | 2.39 m; 2.04 m | 35.6 t | 2.30 m; 2.00 m | 36.3 t | 2.35 m; 2.05 m | 35.4 t | 2.20 m; 1.90 m |
10′ | 26.7 d | 2.85 m | 25.2 d | 3.21 m | 26.4 d | 2.87 m | 26.1 d | 2.58 m |
11′ | 139.7 s | 139.2 s | 139.4 s | 140.1 s | ||||
12′ | 169.4 s | 169.9 s | 169.8 s | 170.2 s | ||||
13′ | 118.9 t | 6.25 d (3.1); 5.60 d (2.8) | 119.7 t | 6.20 d (3.2); 5.55 d (2.9) | 119.6 t | 6.21 d (3.3); 5.55 d (3.0) | 118.4 t | 6.11 d (3.3); 5.44 d (3.1) |
14′ | 18.9 q | 1.21 d (7.1) | 18.7 q | 1.07 d (7.2) | 18.9 q | 1.20 d (7.2) | 18.6 q | 1.05 d (8.3) |
15′ | 13.7 q | 1.76 s | 13.7 q | 1.81 d (1.5) | 13.7 q | 1.78 s | 13.5 q | 1.83 d (1.6) |
2-OAc | 170.7 s | 170.4 s | 170.3 s | |||||
21.1 q | 2.01 s | 21.5 q | 2.04 s | 21.5 q | 2.04 s | |||
2′-OH | 6.34 d (9.8) | 6.18 d (9.3) | ||||||
2′-OAc | 170.6 s | 169.5 s | ||||||
21.2 q | 2.09 s | 21.3 q | 2.06 s |