Abstract
A stereoselective glycosidation with thioglycosides was effected under mild and neutral conditions by combined use of N-bromosuccinimide (NBS) and a catalytic amount of various strong acid salts. A combination of NBS with Ph 2IOTf, Bu 4NOTf, or Bu 4NClO 4 was advantageous for β-selective glucosidation with 2- O-acylated or 2- O-benzylated donors by virtue of either the neighboring group participation or the known solvent effect of nitrile, respectively. α-Selective glucosidation was effected by the use of a 2- O-benzylated donor in the presence of LiClO 4 or LiNO 3 as a catalyst in ether. Addition of silica gel to the reaction mixture increased both the α-selectivity and reaction rate.
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