4.4 Article

RuCl3•3H2O as catalyst for Ferrier rearrangement: an efficient procedure for the preparation of pseudoglycosides

Journal

TETRAHEDRON
Volume 69, Issue 47, Pages 10045-10051

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.09.061

Keywords

Type I Ferrier Rearrangement; RuCl3 center dot 3H(2)O; Tri-O-acetyl-D-glucal; 3,4-Di-O-acetyl-6-deoxy-L-glucal; 2,3-Unsaturated glycoside

Funding

  1. National Natural Science Foundation of China (NSFC) [21272305]
  2. Natural Science Foundation of Shanghai Municipality [12ZR1400200]
  3. Fundamental Research Funds for the Central Universities

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By using RuCl3 center dot 3H(2)O as catalyst, an improved method for the synthesis of 2,3-unsaturated-glycosides has been established. A series of 2, 3-unsaturated-glucosides were obtained from 2,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-6-deoxy-L-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.

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