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Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite

Venkateswarlu, Cheerladinne and Gautam, Vibha and Chandrasekaran, Srinivasan (2014) Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite. In: CARBOHYDRATE RESEARCH, 396 . pp. 48-53.

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Official URL: http://dx.doi.org/ 10.1016/j.carres.2014.07.011

Abstract

A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-beta-D-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved. (C) 2014 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 15 Oct 2014 04:59
Last Modified: 15 Oct 2014 04:59
URI: http://eprints.iisc.ac.in/id/eprint/50014

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