2‐Acetamido‐2‐deoxy‐<scp>l</scp>‐iminosugar <i>C</i>‐Alkyl and <i>C</i>‐Aryl Glycosides: Synthesis and Glycosidase Inhibition

Abstract

The synthesis of a series of six‐membered 2‐acetamido l ‐iminosugar C ‐alkyl and C ‐aryl glycosides is reported. A diastereoselective sugar‐ring enlargement/ C ‐alkylation (or arylation) /ring‐contraction sequence applied to d ‐ gluco ‐ and d ‐ manno ‐configured 2‐acetamido azidolactols provides new l ‐iminosugar C ‐glycosides. The 1,2‐ trans stereocontrolled introduction of the pseudoanomeric substituent in these heterocycles strongly suggests a NHAc neighbouring‐group participation. In their deprotected form, the nine iminosugars exhibit moderate hexosaminidases and β‐glucuronidase inhibition.