Table 2. Reaction of Glycals 1b–1f, 4a, 4b and 5 with Model Glycoside Acceptor 2a.
entry | R1 | R2 | R3 | product (time (h)) | yield (%)a | α:βb | |
---|---|---|---|---|---|---|---|
1 | 1b | Bn | Bn | Ac | 6b (0.7) | 94 | >30:1 |
2 | 1c | Bn | Bn | TIPS | 6c (3) | 65 | 6:1 |
3 | 1d | MOM | MOM | MOM | 6d (6) | 76 | >30:1 |
4 | 1e | TBS | TBS | TBS | 6e (2) | 78 | >30:1 |
5 | 1f | Ac | Ac | Ac | 6f (−) | – | N/A |
6 | 4a | O[Si(i-Pr)2]2 | Bn | 7a (3) | 78 | >30:1 | |
7 | 4b | O[Si(i-Pr)2]2 | TIPS | 7b (2) | 83 | >30:1 | |
8 | 5 | O[Si(i-Pr)2]2 | – | 8 (1) | 91 | 5:1 |
Isolated yield.
Determined by 1H NMR. N/A = not applicable.