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A novel synthesis of N-acetyl-α-D-fucosamine 1-phosphate and uridine 5′-diphospho-N-acetyl-α-D-fucosamine

Lookup NU author(s): Dr Petr Illarionov

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Abstract

In connection with studies on the biosynthesis of capsular polysaccharides from Staphylococcus aureus, a new synthesis of uridine 5′'-(2-acetamido-2,6-dideoxy-α-D-galactopyranosyl diphosphate) (uridine 5′-diphospho-N-acetyl-α-D-fucosamine) using 2-azido-3,4-di-0-acetyl-2,6-dideoxy-α-D-galactopyranosyl nitrate as the key intermediate was carried out. The reaction of this product with cesium dibenzyl phosphate smoothly affords the corresponding β-glycosyl dibenzyl phosphate, which undergoes anomerization on treatment with BF3 • Et2O and 2-bromopyridine to give α-glycosyl dibenzyl phosphate in high yield. This product was then transformed into 2-amino-3,4-di-0-acetyl-2,6-dideoxy-α-D-galactopyranosyl phosphate, subsequently converted into 2-acetamido-2,6-dideoxy-α-D-galactopyranosyl phosphate and the target nucleoside diphosphate sugar.

Publication metadata

Author(s): Illarionov PA, Torgov VI, Hancock II, Shibaev VN

Publication type: Article

Publication status: Published

Journal: Russian Chemical Bulletin

Year: 2001

Volume: 50

Issue: 7

Pages: 1303-1308

Print publication date: 01/01/2001

ISSN (print): 1066-5285

ISSN (electronic): 1573-9171

Publisher: Springer

URL: http://dx.doi.org/10.1023/A:1014035613269

DOI: 10.1023/A:1014035613269

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