Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides.
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.
Paul
Somak
S
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
Jayaraman
Narayanaswamy
N
D002236:Carbohydrate Conformation; D002563:Cerium; D003837:Deoxy Sugars; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry
D003837:Deoxy Sugars; D007202:Indicators and Reagents; D013865:Thioglycosides; D002563:Cerium; C004653:ceric ammonium nitrate