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Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach
Authors:Hiroshi Tanaka
Affiliation:Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan
Abstract:We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl ether. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields.
Keywords:Glycosyl amino acids   One-pot glycosylation   Glycopeptides   Glycosyl fluorides   Oligosaccharide
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