Synlett 1994; 1994(9): 705-708
DOI: 10.1055/s-1994-22978
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Convenient Methods for the Synthesis of ß-C-Glycosyl Aldehydes

M. Elena Lasterra Sánchez* , Veronique Michelet, Isabelle Besnier, Jean Pierre Genêt
  • *Ecole Nationale Supérieure de Chimie de Paris, Laboratoire de Synthèse Organique, Associé au CNRS, 11 rue Pierre et Marie Curie, Paris Cedex 05, France.
Further Information

Publication History

Publication Date:
18 September 2002 (online)

Two methods for the stereoselective ß-formylation at the anomeric carbon of three saccharides are described. In Method A the formyl group is introduced on the starting lactone by a dithiane ring which, after stereospecific reductive dehydroxylation, is hydrolysed to generate the ß-glycosyl aldehyde. In Method B the aldehyde is prepared by introduction of phenylacetylene followed by stereospecific reductive dehydroxylation, partial hydrogenation and subsequent ozonolysis.