405218-92-0Relevant articles and documents
A novel synthesis of N-acetyl-α-D-fucosamine 1-phosphate and uridine 5′-diphospho-N-acetyl-α-D-fucosamine
Illarionov,Torgov,Hancock,Shibaev
, p. 1303 - 1308 (2001)
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.
