Browse by author
Lookup NU author(s): Dr Petr Illarionov
Full text for this publication is not currently held within this repository. Alternative links are provided below where available.
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.
Author(s): Illarionov PA, Torgov VI, Hancock II, Shibaev VN
Publication type: Article
Publication status: Published
Journal: Russian Chemical Bulletin
Print publication date: 01/01/2001
ISSN (print): 1066-5285
ISSN (electronic): 1573-9171
Altmetrics provided by Altmetric