Table 1.
Entry | Procedure | Glycosyl donor | Solvent | Promoter | Product | Yield (%) |
1 | normal | 2a (α) | CH2Cl2/Et2O | AgOTf | 6a | 30 |
2 | reverse | 2a (α) | CH2Cl2/Et2O | AgOTf | 6a | 77 |
3 | reverse | 2a (α) | CH2Cl2 | AgOTf | ― | ― |
4 | reverse | 2b (α) | CH2Cl2/Et2O | AgOTf | 6b | 98 |
5 | normal | 2c (α + β) | CH2Cl2/Et2O | AgOTf | 6c | 51 |
6 | reverse | 2c (α + β) | CH2Cl2/Et2O | AgOTf | 6c | 55 |
7 | reverse | 2c (α + β) | CH2Cl2 | AgOTf | 6c | 90 |
8 | normal | 2d (α + β) | CH2Cl2/Et2O | AgOTf | 6d | 73 |
9 | reverse | 2d (α + β) | CH2Cl2 | AgOTf | 6d | 93 |
10 | reverse | 3a (α) | CH2Cl2/Et2O | AgOTf | 6a | 69 |
11 | reverse | 3b (α) | CH2Cl2/Et2O | AgOTf | 6b | 86 |
12 | reverse | 3c (β) | CH2Cl2 | AgOTf | 6c | 99 |
13 | reverse | 3d (β) | CH2Cl2 | AgOTf | 6d | 87 |
14 | normal | 5a (α + β) | CH2Cl2 | TMSOTf | 6a | 85 |
15 | normal | 5b (α + β) | CH2Cl2 | TMSOTf | 6b | 81 |
16 | normal | 5c (β) | CH2Cl2 | TMSOTf | 6c | 83 |
17 | normal | 5d (β) | CH2Cl2 | TMSOTf | 6d | 52 |