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The synthesis of N-acetyl-β-L-fucosamine-1-phosphate and uridine 5′-diphospho-N-acetyl-β-L-fucosamine

Lookup NU author(s): Dr Petr Illarionov, Dr Ian Hancock


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Uridine 5′-(2-acetamido-2,6-dideoxy-β-L-galactopyranosyl) diphosphate (uridine 5′-diphospho-N-acetyl-β-L-fucosamine) was synthesized. The key intermediate, 3,4-di-O-acetyl-2-azido-2,6-dideoxy-β-L-galactopyranosyl dibenzyl phosphate, was prepared by a previously unknown reaction of cesium dibenzyl phosphate with the corresponding α-glycosyl nitrate and was then converted into the N-acetylated glycosyl phosphate and nucleoside diphosphate sugars via 3,4-di-O-acetyl-2-amino-2,6-dideoxy-β-L-galactopyranosyl phosphate using mild N-acetylation and O-deacetylation as the last synthetic steps.

Publication metadata

Author(s): Hancock I; Illarionov PA; Torgov VI; Shibaev VN

Publication type: Article

Publication status: Published

Journal: Russian Chemical Bulletin

Year: 2000

Volume: 49

Issue: 11

Pages: 1891-1894

ISSN (print): 1066-5285

ISSN (electronic): 1573-9171

Publisher: Springer New York LLC