Table 1. Effect of Sulfonylating Agenta.
entry | sulfonylating agent | yield (%)b | β/α ratioc |
---|---|---|---|
1 | 4a | 27 | β only |
2 | 4b | 29 | β only |
3 | 4c | 29 | β only |
4 | 4d | 36 | β only |
5 | 4e | 27 | β only |
6 | 4f | 36 | β only |
7 | 4g | 29 | β only |
8 | 4h | 18 | β only |
9 | 4i | 46 | β only |
10 | 4j | 15 | β only |
11 | 4k | 17 | β only |
0.20 mmol of glucosyl donor 1, 0.13 mmol of acceptor 2, 0.20 mmol of TTBP, 0.20 mmol of sulfonylating agent, THF as the solvent, 2 h of activation time. Glycosylation [1] = 0.050 M.
Isolated yield.
All selectivities based on 1H NMR analysis of purified material (see SI). TTBP = 2,4,6-tri-tert-butylpyrimidine.