An improved method for the syntheses of p-aminophenyl 1-thio-beta-D-glycosides

The condensation of the appropriate acetylglycosyl bromides with p-aminobenzenethiol in the presence of sodium methoxide afforded p-aminophenyl 1-thio-beta-D-glucopyranoside, 1-thio-beta-D-galactopyranoside, 1-thio-beta-D-xylopyranoside, and 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranoside. p-Aminophenyl 1-thio-beta-D-glucopyranosiduronic acid was synthesized by condensation of methyl (2,3,4-tri-O-acetyl-alpha-D-glucopyranosyl bromide)uronate with p-aminobenzenethiol, followed by saponification with sodium hydroxide.