Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Monoacetylation of Carbohydrate Diols via Transesterification with Ethyl Acetate

Xuyu Liu A , Bernd Becker A B and Matthew A. Cooper A B
+ Author Affiliations
- Author Affiliations

A Institute for Molecular Bioscience, University of Queensland, Brisbane, Queensland 4072, Australia.

B Corresponding authors. Email: bbeckerr@gmail.com; m.cooper@uq.edu.au

Australian Journal of Chemistry 67(4) 679-683 https://doi.org/10.1071/CH12518
Submitted: 21 November 2012  Accepted: 2 January 2014   Published: 13 February 2014

Abstract

Monoacetylation of secondary diols in protected monosaccharides was achieved with ethyl acetate as acyl donor and sodium tert-butoxide as a base. The regioseletivity of the reaction varied depending on the substrate. This new method provides a simple, fast, and efficient method to access selectively acetylated carbohydrates that is compatible with acid-sensitive protecting groups.


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