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Synthesis of morphine 6-α-d-glucuronide

✍ Scribed by Igor Rukhman; Arie L Gutman

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
108 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

This paper provides the ®rst report on stereoselective synthesis and characterization of morphine 6-a-dglucuronide (M6aG), useful as a reference marker for testing the purity and stability of the pharmaceutically important morphine 6-b-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 a/b stereoselectivity of the reaction can be directed and controlled by the amount of zinc bromide.

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