, Volume 50, Issue 7, pp 1303-1308

A novel synthesis of N-acetyl-α-d-fucosamine 1-phosphate and uridine 5"-diphospho-N-acetyl-α-d-fucosamine

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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-O-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-O-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.