✦ LIBER ✦

Synthesis of C-glycosides of N-acetylglucosamine by direct alkylation of 2-amino-2-deoxy-2,3,4,6-tetra-O-acetyl glucopyranosyl chloride

✍ Scribed by Kyung-Il Kim; Rawle I. Hollingsworth

Book ID: 104216314
Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 156 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)79957-6

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✦ Synopsis

The B-isomer of C-glycoside, ethyl 2-aceta~no-2-~oxy-3,4,6-~-O-ace~l-~-D-glucopyranosylacetateQ) was prepared stenoselectively in two steps by reaction of 2-acetamino-2-deoxy-3,4X&i-O-acetyl-a-D-glucopyranosyl chloride(&) with potassium diethylmalonate and 18-crown-6, followed by decarboxylation. C-Glycoside formation of carbohydrates becomes more interesting to carbohydrate chemists and biochemists, not only for the preparation of useful synthetic intermediates but also for the synthesis of carbohydrate biological probes which are inert to 0-glycosidic bond cleavage by glycosidases. Though syntheses of N-acetylglucosamine C-glycosides such as 1 and 2 have been reportedQ for use in the pmparation of lipid A

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