Glycosylation with N-Troc-protected glycosyl donors |
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Authors: | Ulf Ellervik,Gö ran Magnusson |
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Affiliation: | Organic Chemistry 2, Chemical Center, The Lund Institute of Technology, University of Lund, P.O. Box 124, S-221 00, Lund, Sweden |
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Abstract: | N-Troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, methyl 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl . The N-Troc-protected donors gave pure β-glycosides in somewhat higher yields than the N-Phth-protected counterparts. The N-Troc protecting group can be removed by reduction with zinc, which allows selective N-deprotection in oligosaccharides containing both N-Troc and N-Phth groups. |
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Keywords: | N-Troc-protected glycosyl donors Glycosylation |
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