Thioglycosylation of 1,2-cis-glycosyl acetates: a long-standing overlooked issue in preparative carbohydrate chemistry

Abstract

1,2-cis-Glycosyl acetates with the α-configuration were revealed to be very unreactive towards Lewis acid catalyzed thioglycosylations. Optimal and cost-effective conditions for enabling this direct conversion is absent in the literature. Our studies have shown that elevating the reaction temperature with a catalytic amount of BF(3)·OEt(2) was more effective than changing Lewis acids with higher acidities to accommodate the low reactivity of α-glycosyl acetates. The effect of impurities in stored BF(3)·OEt(2) on the reaction is also discussed.