Synthesis of 2‐Acetamido‐2‐deoxy‐<scp>D</scp>‐gluconhydroximolactone‐ and Chitobionhydroximolactone‐Derived <i>N</i>‐Phenylcarbamates, Potential Inhibitors of β‐<i>N</i>‐Acetylglucosaminidase

Abstract

Abstract The N ‐phenylcarbamate 7 , derived from 2‐acetamido‐2‐deoxy‐ D ‐gluconhydroximo‐1,5‐lactone ( 3 ) and the analogous N ‐phenylcarbamate 14 , derived from chitobionhydroximo‐1,5‐lactone ( 10 ) have been prepared as potential inhibitors of β‐ N ‐acetylglucosaminidases. The unambiguous synthesis of the hydroximo‐1,5‐lactone 3 involves oxidation of the oxime 1 , followed by deprotection with Na/NH 3 .