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Alkylation-initiated glycosidation of benzoylated thioimidates 6-8
 | ||||
|---|---|---|---|---|
| entry | donor | Promoter (equiv, temp) | time | product 9 (yield, α/β) |
| 1 | 6 | MeOTf (3, rt) | 2 h | (97%, β only) |
| 2 | 7 | MeOTf (3, rt) | 1 h | (95%, β only) |
| 3 | 8 | MeOTf (3, rt) | 2 h | (84%, β only) |
| 4 | 6-8 | MeI (9-15, rt) | 120 h | No reaction |
| 5 | 6 | BnBr (3, 55 °C) | 72 h | (79%, β only) |
| 6 | 7 or 8 | BnBr (3-9, 55°C) | 120 h | no reaction |
