Table 1.
C/H | 5 | 6 | 7 | 8 | ||||
---|---|---|---|---|---|---|---|---|
1 | 35.6 t | 1.22 m 1.34 m |
35.6 t | 0.94 m 1.34 m |
33.5 t | 1.10 m 1.35 m |
34.9 t | 1.22 m 1.40 m |
2 | 33.8 t | 1.57 m 1.76 m |
33.8 t | 1.20 m 1.73 m |
28.2 t | 1.99 m 2.05 m |
33.8 t | 1.54 m 1.76 m |
3 | 77.6 s | 76.6 s | 77.0 s (78.7) * |
77.3 s | ||||
4 | 41.8 s | 41.8 s | 42.0 s | 42.6 s | ||||
5 | 51.3 d | 1.38 m | 51.7 d | 1.40 m | 53.5 d (54.5) * |
1.08 m | 54.6 d | 1.08 m |
6 | 21.3 t | 1.41 m 1.50 m |
19.9 t | 1.41 m 1.47 m |
20.00 t | 1.27 m 1.40 m |
20.3 t | 1.45 m 1.50 m |
7 | 31.6 t | 1.30 m 1.32 m |
31.6 t | 1.29 m 1.37 m |
33.3 t | 0.83 m 0.90 m |
31.6 t | 1.20 m 1.42 m |
8 | 37.9 s | 37.8 s | 37.6 s | 38.1 s | ||||
9 | 47.6 d | 1.76 m | 47.7 d | 1.73 m | 46.8 d | 1.60 m | 47.7 d | 1.70 m |
10 | 37.9 s | 37.9 s | 37.7 s | 38.3 s | ||||
11 | 24.1 t | 1.92 m 1.93 m |
24.4 t | 1.89 m 1.91 m |
23.8 t | 1.80 m 1.96 m |
24.5 t | 1.91 m 1.95 m |
12 | 123.5 d | 5.28 t (3.15) |
123.7 d | 5.26 t (3.3) |
122.4 d | 5.39 t (3.2) |
123.6 d | 5.27 t (3.1) |
13 | 145.1 s | 145.2 s | 144.9 s | 145.2 s | ||||
14 | 40.5 s | 40.8 s | 37.8 s | 40.6 s | ||||
15 | 28.8 t | 1.10 m 1.81 m |
28.8 t | 1.10 m 1.78 m |
31.01 t | 1.24 m 1.70 m |
29.0 t | 1.08 m 1.82 m |
16 | 24.4 t | 1.61 m 2.03 m |
24.5 t | 1.59 m 2.02 m |
26.1 t | 0.99 m 1.00 m |
24.1 t | 1.64 m 2.04 m |
17 | 43.0 s | 43.0 s | 42.2 s | 42.9 s | ||||
18 | 42.7 d | 2.88 dd (13.9, 4.4) | 42.7 d | 2.86 dd (14.0, 4.5) |
39.8 d | 3.20 dd (13.6, 4.5) |
42.8 d | 2.87 dd (13.7, 4.7) |
19 | 47.2 t | 1.14 m 1.70 m |
47.3 t | 1.12 m 1.67 m |
46.7 t | 1.21 m 1.69 m |
47.3 t | 1.16 m 1.71 m |
20 | 29.5 s | 29.9 s | 28.7 s | 30.8 s | ||||
21 | 34.9 t | 1.22 m 1.34 m |
34.9 t | 0.95 m 1.33 m |
34.9 t | 1.08 m 1.33 m |
34.7 t | 1.22 m 1.35 m |
22 | 34.1 t | 1.56 m 1.77 m |
34.1 t | 1.55 m 1.75 m |
34.8 t | 1.03 m 1.24 m |
34.2 t | 1.55 m 1.77 m |
23 | 17.7 q | 0.84 s | 17.7 q | 0.83 s | 23.8 q | 1.01 s | 24.6 q | 0.90 s |
24 | 19.9 q | 0.82 | 24.0 q | 0.91 s | 19.4 q | 1.05 s | 20.0 q | 0.92 s |
25 | 15.0 q | 0.97 s | 15.5 q | 0.92 s | 16.1 q | 0.85 s | 16.2 q | 1.02 s |
26 | 17.8 q | 0.96 s | 17.8 q | 0.83 s | 17.5 q | 0.92 s | 17.9 q | 0.86 s |
27 | 26.5 q | 1.22 s | 26.4 q | 1.19 s | 24.7 q | 1.10 s | 26.1 q | 1.22 s |
28 | 181.8 s | 181.9 s | nd | 181.8 s | ||||
29 | 33.5 q | 0.94 s | 33.6 q | 0.95 s | 31.0 q | 0.85 s | 33.2 q | 0.95 s |
30 | 24.0 q | 0.97 s | 24.0 q | 0.95 s | 23.8 q | 0.92 s | 24.0 q | 0.98 s |
1′ | 38.0 t | 1.47 m 1.78 m |
40.5 t | 1.42 m 1.84 m |
34.8 t | 1.93 m 2.29 m |
37.8 t | 1.62 m 1.92 m |
2′ | 70.3 d | 4.04 d quint. (1.8, 5.4) | 69.6 d | 3.94 m | 70.8 d | 4.42 quint. (5.3) |
70.3 d | 3.92 quint. (5.7) |
3′ | 67.8 t | 3.49 dd (5.7, 10.6) 3.44 dd (5.6, 10.6) |
68.6 t | 3.48 dd (5.1, 10.9) 3.44 dd (6.4, 10.8) |
68.2 t | 3.93 dd (5.8, 10.6) 3.83 dd (5.11, 10.7) |
68.6 t | 3.49 dd (11.7, 6.8) 3.58 dd (11.6, 6.8) |
1 Data collected in MeOH-d4 for compounds 5, 6, and 8, in Py-d5 for 7. * Data in parentheses are the values obtained for compound 7 in MeOH-d4, where it is sparingly soluble. Hence, the complete characterization of 7 was made in Py and a decoupled 13C NMR spectrum was registered in methanol in order to compare the signals necessary for the stereochemical analysis.