Synthesis of 2‐Acetamido‐2‐deoxy‐ D ‐gluconhydroximolactone‐ and Chitobionhydroximolactone‐Derived N‐Phenylcarbamates, Potential Inhibitors of β‐N‐Acetylglucosaminidase

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/NH3.