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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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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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