The use of Benzyl Esters in the Synthesis of 1ß-O-Acyl Glucuronides by Selective Acylation

Introduction

Acyl glucuronides are key phase 2 metabolites for many carboxylic acid-containing drugs, notably of non-steroidal anti-inflammatory agents (NSAIDs).¹It is important to synthesise acyl glucuronides in pure form, and especially as single 1ß-anomers, for bioevaluation during drug discovery and development. Acyl glucuronides are reactive species: they may react by hydrolysis or displacement with other nucleophiles or by acyl migration followed by condensation with amines.