Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides

Paul, Somak and Jayaraman, Narayanaswamy (2004) Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides. In: Carbohydrate Research, 339 (13). pp. 2197-2204.

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Abstract

Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Apart from the 2-deoxy-1-thioglycosides, formation of the 2,3-unsaturated enose, corresponding to the Ferrier product, is also observed, especially for the glucal substrates. A radical oxocarbenium ion and a thiolate intermediates are most likely to mediate the reaction. Upon synthesis of 2-deoxy-1-thioglycosides, few representative glycosylation reactions with both aglycosyl and glycosyl acceptors were performed and \alpha-anomeric 2-deoxy glycosides were obtained exclusively.

Item Type:	Journal Article
Publication:	Carbohydrate Research
Publisher:	Elsevier
Additional Information:	The Copyright belongs to Elsevier.
Keywords:	Carbohydrates;Deoxysugars;Enoses;Thioglycosides
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	17 Apr 2006
Last Modified:	19 Sep 2010 04:25
URI:	http://eprints.iisc.ac.in/id/eprint/6303

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