Ruthenium trichloride catalyzed synthesis of 2,3-unsaturated-N-glycosides via Ferrier azaglycosylation |
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Authors: | Thurpu Raghavender Reddy Sravanthi ChittelaSudhir Kashyap |
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Institution: | D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, AP, India |
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Abstract: | An efficient, economical and mild protocol for the synthesis of 2,3-unsaturated-N-glycosides has been developed using ruthenium(III) chloride. The Ferrier azaglycosylation of glycals with various N-nucleophiles such as sulfonamides, benzamides, carbamates and N-substituted sulfonamides proceeded smoothly to afford the corresponding 2,3-unsaturated-N-glycosides or ‘N-pseudoglycals’ in good yields (64–98%). High α-anomeric selectivity was observed with N-substituted sulfonamides such as N-benzyl or N-phenyl sulfonamides under similar conditions. |
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Keywords: | Azaglycosylation 2 3-Unsaturated-N-glycosides Tri-O-acetyl-d-glucal Sulfonamides Ruthenium trichloride |
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