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Synlett 1994; 1994(9): 705-708
DOI: 10.1055/s-1994-22978
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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.
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Publication Date:
18 September 2002 (online)

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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.