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|
|Additional Information:||The Copyright belongs to Elsevier.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||17 Apr 2006|
|Last Modified:||19 Sep 2010 04:25|
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