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. 2019 Sep 24;141(42):16743–16754. doi: 10.1021/jacs.9b07022

Table 1. Effect of Sulfonylating Agenta.

graphic file with name ja9b07022_0005.jpg

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
a

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.

b

Isolated yield.

c

All selectivities based on 1H NMR analysis of purified material (see SI). TTBP = 2,4,6-tri-tert-butylpyrimidine.