G. Bedi, R. H. Shah, O. P. Bahl
May 1, 1978
Citations
0
Influential Citations
6
Citations
Journal
Carbohydrate Research
Abstract
Abstract The acetamido group of p -nitrophenyl 2-acetamido-2-deoxy-β- d -glucopyranoside, -β- d -galactopyranoside, and their 1-thio analogs was modified by replacement of the amide-carbonyl oxygen atom with sulfur by treatment of their fully acetylated derivatives with phosphorus pentasulfide in pyridine. The resulting p -nitrophenyl 2-deoxy-2-thioacetamido-β- d -hexopyranoside triacetates were O -deacetylated with catalytic amounts of sodium methoxide in methanol to obtain p -nitrophenyl 2-deoxy-2-thioacetamido-β- d -glucopyranoside, -β- d -galactopyranoside, and their 1-thio analogs. These derivatives inhibited 2-acetamido-2-deoxy-β- d -glucosidase from Turbatrix aceti to various extents. Also obtained in significant yields in the aforementioned reaction with phosphorus pentasulfide in pyridine were the two hitherto unreported thiazolines, namely, 2-methyl(2-acetamido-3,4,6-tri- O -acetyl-α- d -glucopyrano)[2′,1′:4,5]-2-thiazoline and 2-methyl(2-acetamido-3,4,6-tri- O -acetyl-α- d -galactopyrano)[2′,1′:4,5]-2-thiazoline.