Igor Rukhman

Selective synthesis of both isomers of morphine 6-β-d-glucuronide and their analogs

Abstract A stereoselective synthesis of both isomers of the pharmaceutically important morphine 6-β- d -glucuronide (M6G) and its analogs was developed. The method is based on the use of ZnBr2 for the key coupling reaction. It was shown that the α/β stereoselectivity of the reaction can be directed and controlled by the amount of ZnBr2. This paper describes the synthesis, analysis and characterization of the α-isomer of M6G, useful as a reference marker for testing purity and stability of the morphine 6-β- d -glucuronide (M6G).

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.