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Catalytic and regioselective oxidation of carbohydrates to synthesize keto-sugars under mild conditions.

Authors
  • Muramatsu, Wataru
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Sep 19, 2014
Volume
16
Issue
18
Pages
4846–4849
Identifiers
DOI: 10.1021/ol502344h
PMID: 25198882
Source
Medline
License
Unknown

Abstract

A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA](+)Br3(-)) accelerates the regioselective oxidation at the "axial"-OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.

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