M. Wolfrom, H. B. Bhat, P. Conigliaro
Dec 1, 1971
Citations
0
Influential Citations
7
Citations
Journal
Carbohydrate research
Abstract
Abstract 2-Deoxy-2-(p-methoxybenzylidene)amino- D -galactose was acetylated, and the resulting product was treated with hydrochloric acid, giving 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β- D -galactopyranose hydrochloride (3). Treatment of 3 with trifluoroacetic anhydride yielded 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(trifluoroacetamido)-β- D -galactopyranose (4), which was converted into 3,4,6-tri-O-acetyl-2-deoxy-2-(trifluoroacetamido)-α- D -galactopyranosyl bromide (5) by a previously published procedure. Condensation of 5 with bis(trimethylsilyl)cytosine yielded 1-[3,4,6-tri-O-acetyl-2-deoxy-2-(trifluoroacetamido)-β- D -galactopyranosyl]cytosine, which was deacylated with methanolic ammonia to give 1-(2-amino-2-deoxy-β- D -galactopyranosyl)cytosine. Condensation of 5 with bis(trimethylsilyl)thymine yielded 1-[3,4,6-tri-O-acetyl-2-deoxy-2-(trifluoroacetamido)-β- D -galactopyranosyl]thymine (8), which was deacylated with methanolic ammonia to give 1-(2-amino-2-deoxy-β- D -galactopyranosyl)thymine (9). Condensation of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α- D -galactopyranosyl chloride with bis(trimethylsilyl)thymine gave 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β- D -galactopyranosyl)thymine (11), but in substantially lower yield than 8. Compound 11 was also obtained by acetylation of 9.