Stereoselectivity in the oxidation of 5-thioglucose derivatives with 3-chloroperoxybenzoic acid.

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概要

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• 5-Thio-α-D-glucopyranose derivatives were oxidized with 3-chloroperoxybenzoic acid in various conditions to give axial and equatorial sulfoxides. Structure of an axial sulfoxide obtained was determined by X-ray crystallography. Configuration of other sulfoxides was determined by <SUP>1</SUP>HNMR spectroscopy according to empirical rules of chemical shift. The anomeric substituent was decisive for the stereoselectivity and the ratios of axial to equatorial sulfoxide were 3–11.5 for methoxy derivatives and 0.4–1.0 for acetoxy derivatives.

• 公益社団法人 日本化学会の論文

著者

• Takenaka Akio

  Department of Life Science, Faculty of Science, Tokyo Institute of Technology

• Yuasa Hideya

  Department of Life Science, Faculty of Science, Tokyo Institute of Technology

関連論文

• Stereoselectivity in the oxidation of 5-thioglucose derivatives with 3-chloroperoxybenzoic acid.

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