Synthesis 2006(9): 1499-1503  
DOI: 10.1055/s-2006-926422
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C-Glucoside endo-Glycals from C-Glucosyl Vinyl Sulfones

David Gueyrard*, Patrice Fontaine, Peter G. Goekjian
UMR 5181, Laboratoire de Chimie Organique 2 - Glycochimie, Université Claude Bernard Lyon 1, CNRS, 43, bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France
Fax: +33(4)23238349; e-Mail: david.gueyrard@univ-lyon1.fr;
Further Information

Publication History

Received 12 December 2005
Publication Date:
07 April 2006 (eFirst)

Abstract

The synthesis and the reactivity of C-glucosyl vinyl sulfones in two steps from benzylated gluconolactone and benzothi­azolylsulfones derivatives is reported.

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11

The configuration of the double bond has been determined by NOE experiments. A correlation has been observed between the vinylic proton and H-2.