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Synthesis of Aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides

Paul, Somak and Jayaraman, Narayanaswamy (2007) Synthesis of Aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides. In: Carbohydrate Research, 342 (10). pp. 1305-1314.

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Abstract

The synthesis of either anomers of aryl 2-deoxy-D-glycopyranosides from 2-deoxy-1-thioglycosides is reported. The $\alpha$-anomers form as the major product when thioglycosides react with differently substituted phenols and naphthols, in the presence of N-iodosuccinimide/triflic acid. On the other hand, reaction of the thioglycosides with bromine initially, followed by reaction with aryloxy anions lead to aryl 2-deoxy-$\beta$-D-glycosides with high specificities.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier.
Keywords: Aryl glycosides;Deoxysugars;Glycosylations;Thioglycosides
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 19 Sep 2007
Last Modified: 19 Sep 2010 04:39
URI: http://eprints.iisc.ernet.in/id/eprint/11821

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