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De novo synthesis of 1-deoxythiosugars

Gunasundari, Thanikachalam and Chandrasekaran, Srinivasan (2013) De novo synthesis of 1-deoxythiosugars. In: Carbohydrate Research, 382 . pp. 30-35.

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Official URL: http://dx.doi.org/10.1016/j.carres.2013.09.009


A short and efficient chemical synthesis of biologically potent and novel 1-deoxythiosugars is accomplished. Introduction of sulfur mediated by benzyltriethylammonium tetrathiomolybdate, as a sulfur transfer reagent through nucleophilic double displacement of tosylate in alpha,omega-di-O-tosyl aldonolactones in an intramolecular fashion is the key feature. The subsequent reduction of thiosugar lactones with borohydride exchange resin (BER) offers a number of deoxythiosugars in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Publication: Carbohydrate Research
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Keywords: Tetrathiomolybdate; 1-Deoxythiosugars; Aldonoditosylate; Thiosugar Lactone; Borohydride Exchange Resin
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 10 Jan 2014 08:29
Last Modified: 10 Jan 2014 08:29
URI: http://eprints.iisc.ac.in/id/eprint/48097

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