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1. Synthetic studies toward pyruvate acetal containing saccharides: synthesis of the carbohydrate part of Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens

Author

Ziegler, Thomas, Eckhardt, Elisabeth, and Birault, Veronique

Subjects
Organic compounds -- Synthesis, Carbohydrates -- Research, Glycosylation -- Research, Glycosides -- Research, Biological sciences, Chemistry
Abstract

Seven 4,6-O-pyruvylated D-glucosyl donors undergo glycosylation studies with methanol and methyl 2,4,6-tri-O-benzoyl-beta-D-glucopyranoside. The best yields and beta-selectivity are obtained with the trichloroacetimidate catalyzed by trimethylsilyl triflate. The studies form the basis of the synthesis of the carbohydrate moiety of the lipopentasaccharide of Mycobacterium smegmatis and its smaller fragments from pyruvylated 3-O-methyl-D-glucosyl imidate.

Published
1993

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