Preparation and reductive lithiation of 2-deoxy-D-glucopyranosyl phenylsulfones: A highly stereoselective route to C-glycosides |
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Authors: | Jean-Marie Beau Pierre Sinaÿ |
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Affiliation: | Laboratoire de Biochimie Structurale, U.A. 499, U.E.R. de Sciences Fondamentales et Appliquées, 45046 Orléans Cédex, France |
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Abstract: | 2-Deoxy-D-glucopyranosyl phenylsulfones 3a–c have been synthesized in 75–83% yield from commercial tri-O-acetyl-D-glucal 1. Their reductive desulfonylation by lithium naphthalenide and reaction of the intermediate glycosyl-lithium 5 with aldehydes leads to α-D-C-glucopyranosides with high stereoselectivity. |
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