N. Pravdic, Ivanka Franjić-Mihalić
May 1, 1978
Citations
0
Influential Citations
7
Citations
Journal
Carbohydrate Research
Abstract
Abstract 9-(2-Acetamido-3,4,6-tri- O -acetyl-2-deoxy-β- d -glucopyranosyl)-6-benzamidopurine ( 9 ) and 6-benzamido-9-(2,3,4,6-tetra- O -acetyl-β- d -glucopyranosyl)purine ( 11 ) have been prepared by three synthetic routes: ( a ) the fusion procedure, ( b ) direct condensation of 6-benzamido(chloromercuri)purine with the acetylated chloride, or ( c ) with the chloride formed in situ from the 1-acetate in the presence of titanium tetrachloride. The results obtained are briefly discussed; the direct condensation of the mercuri salt with chlorides proved to be the most convenient. Whereas, in the condensation with acetylated chlorides, only products having the β- d anomeric configuration were isolated, the chloride protected with non-participating groups (benzyl) afforded both anomers. The removal of the benzyl groups should be preceded by hydrolytic cleavage of the benzamido group. A simple procedure for fractionation, on small columns of silica gel, of reaction mixtures obtained in the fusion reactions is described.