Journal
CARBOHYDRATE RESEARCH
Volume 339, Issue 13, Pages 2197-2204Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2004.07.010
Keywords
carbohydrates; deoxysugars; enoses; thioglycosides
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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. (C) 2004 Elsevier Ltd. All rights reserved.
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