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
Publication:	Carbohydrate Research
Publisher:	Elsevier
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.ac.in/id/eprint/11821

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