Glycosidation of 4,5-epoxymorphinan-6-ols

Details Glycosidation of 4,5-epoxymorphinan-6-ols Glycosidation of 4,5-epoxymorphinan-6-ols

C - Chemistry, Metallurgy

07

H

C07H 17/00 (2006.01)

Patent

CA 2319833

Glycosidation of 4,5-Epoxymorphinan-6-ols with a Thioglycoside as a glycoside donor is disclosed. The process comprises reacting a 4,5-Epoxymorphinan-6-ol and a Thioglycoside in the presence of a thiophilic promoter under conditions capable of forming 4,5-Epoxymorphinan-6-glycosides. This novel approach was used for preparation of pharmaceutically important 4,5-Epoxymorphinan-6-.beta.- D-glucuronides. The process provides both high stereo-selectivity and high yields.

L'invention concerne la glycosidation de 4,5-époxymorphinane-6-ols via un thioglycoside tenant lieu de donneur de glycoside. Le procédé consiste à faire réagir un 4,5-époxymorphinane-6-ol et un thioglycoside en présence d'un promoteur thiophile, dans des conditions permettant d'assurer la formation de 4,5-époxymorphinane-6-glycosides. Cette nouvelle approche a été utilisée pour l'élaboration de 4,5-époxymorphinane-6-.beta.-D-glucuronides ayant une fonction pharmaceutique importante. Le procédé considéré offre un haut niveau de stéréosélectivité et de rendement.

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