Synthesis of morphine 6-α- d-glucuronide

Abstract

This paper provides the first report on stereoselective synthesis and characterization of morphine 6-α- d-glucuronide (M6αG), useful as a reference marker for testing the purity and stability of the pharmaceutically important morphine 6-β- d-glucuronide (M6G). The synthesis is based on the glycosylation of 3- O-acetylated morphine with methyl 2,3,4-tri- O-acetyl- d-glucopyranosyluronate bromide as glycosyl donor and zinc bromide as catalyst. Furthermore, we showed that the α/β stereoselectivity of the reaction can be directed and controlled by the amount of zinc bromide.