Table 1.
entry | D | A | time | product | yield, % | α/β ratio |
---|---|---|---|---|---|---|
1 | 1 | 13 | 24 h | 17a | -a | - |
2b | 1 | 13 | 16 h | 17a | 91 | 1.4/1 |
3c | 1 | 13 | 5 h | 17a | 95 | 2.0/1 |
4 | 2a | 13 | 5 min | 17a | 92 | 2.4/1 |
5 | 2b | 13 | 5 min | 17b | 96 | β only |
6 | 2b | 14 | 24 h | 18b | 82 | β only |
7 | 3a | 13 | 10 min | 17a | 89 | 1.2/1 |
8 | 3b | 13 | 10 min | 17b | 91 | β only |
9 | 3b | 14 | 15 min | 18b | 84 | β only |
10 | 3c | 13 | 15 min | 17c | 91 | 1.6/1 |
11 | 4a | 15 | 5 min | 19a | 87 | 7.4/1 |
12 | 4b | 13 | 20 min | 17b | 90 | β only |
13 | 5a | 13 | 5 min | 17a | 95 | 1.3/1 |
14 | 5a | 14 | 5 min | 18a | 92 | 1.4/1 |
15 | 5b | 13 | 10 min | 17b | 90 | β only |
16 | 5c | 13 | 20 min | 17c | 75 | 1.2/1 |
17 | 6 | 13 | 24 h | 17a | -a | - |
18d | 6 | 13 | 24 h | 17a | 91 | 1.2/1 |
19e | 6 | 13 | 10 min | 17a | 92 | 1.2/1 |
20 | 7 | 13 | 24 h | 17a | -a | - |
21d | 7 | 13 | 24 h | 17a | 89 | 1.0/1 |
22e | 7 | 13 | 20 min | 17a | 76 | 1.2/1 |
23 | 8 | 13 | 5 min | 17a | 97 | 1.6/1 |
24 | 8 | 12 | 10 min | 16a | 91 | 1/3.4 |
25 | 9 | 13 | 20 h | 17a | 81 | 2.0/1 |
26 | 9 | 15 | 1.5 h | 19a | 81 | 2.3/1 |
27 | 10 | 13 | 24 h | 17a | -a | - |
28 | 11 | 13 | 5 min | 17a | 80 | 1/1.5 |
29 | 11 | 12 | 2 days | 16a | 65 | 1/5.4 |
no product formation was detected; all glycosylations were promoted with AgBF4 except the following:
3.0 equiv. of BF3-Et2O was used
3.0 equiv. of BF3-Et2O and 0.5 equiv. of AgBF4 was used
2.0 equiv. of NIS was used
2.0 equiv. of NIS and 0.5 equiv. of AgBF4 was used.