Carbohydrate Research 2004-09-13

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

Somak Paul, Narayanaswamy Jayaraman

Index: Carbohydr. Res. 339(13) , 2197-204, (2004)

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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.