Carbohydrate Research 2008-11-24

A facile preparation of peracylated alpha-aldopyranosyl chlorides with thionyl chloride and tin tetrachloride.

Qingbing Wang, Jie Fu, Jianbo Zhang

Index: Carbohydr. Res. 343(17) , 2989-91, (2008)

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Abstract

Aldopyranose peracetates react with thionyl chloride and tin tetrachloride, producing the corresponding peracylated aldopyranosyl chlorides in very good to excellent yields (88-100%) with exclusive alpha-anomeric selectivity and short reaction times. The use of peracylated sugars as the substrate in large scale reactions also proceeds in high yield.