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

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

Carbohydrate Research 346(9): 1149-1153

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.

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Accession: 056560013

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PMID: 21524413

DOI: 10.1016/j.carres.2011.03.033

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