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

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

Carbohydrate research (2008-10-07)
Qingbing Wang, Jie Fu, Jianbo Zhang
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Thionyl chloride, ReagentPlus®, ≥99%
Sigma-Aldrich
Thionyl chloride, reagent grade, 97%
Sigma-Aldrich
Tin(IV) chloride, 98%
Sigma-Aldrich
Tin(IV) chloride solution, 1.0 M in methylene chloride
Sigma-Aldrich
Tin(IV) chloride, 99.995% trace metals basis