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Deoxythiosugar Derivatives with Furano, Pyrano, and Septano Motifs from L-Gulono-1,4-lactone and D-Glycero-D-gulo-heptono-1,4-lactone

Gunasundari, Thanikachalam and Chandrasekaran, Srinivasan (2012) Deoxythiosugar Derivatives with Furano, Pyrano, and Septano Motifs from L-Gulono-1,4-lactone and D-Glycero-D-gulo-heptono-1,4-lactone. In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (35). pp. 6986-6995.

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Official URL: http://dx.doi.org/10.1002/ejoc.201200906

Abstract

A short synthesis of thiosugar derivatives mimicking furanose, pyranose, and septanose structures has been achieved starting from L-gulono-1,4-lactone and D-glucoheptono-1,4-lactone. Different strategies used in the synthesis are: (1) a nucleophilic displacement and Michael addition; (2) epoxide ring opening and Michael addition; (3) epoxide ring opening and nucleophilic displacement process; and (4) double nucleophilic displacement. All of these reactions used benzyltriethylammonium tetrathiomolybdate, (BnEt3N)(2)MoS4 as the sulfur-transfer reagent.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to WILEY-V C H VERLAG GMBH, GERMANY
Keywords: Carbohydrates;Glycomimetics;Sulfur heterocycles;Nucleophilic substitution;Michael addition
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Francis Jayakanth
Date Deposited: 03 Jan 2013 07:23
Last Modified: 03 Jan 2013 07:23
URI: http://eprints.iisc.ac.in/id/eprint/45579

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