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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 3
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Original Articles

Synthesis of Morphine-3-Glucuronide

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Pages 231-236 | Received 07 Feb 1975, Published online: 05 Dec 2006
 

Abstract

Morphine-3-glucuronide [1, morphine-(3β-d-glucopyranosyl)-uronate is a major metabolite of morphine (2a) and heroin (2b) in man and animals.1,2,3 However, due to the lack of the availability of sufficient quantities, the pharmacological and toxicological properties as well as the chemical properties of this metabolite have not been fully evaluated. Yoshimura and co-workers4 reported that 1 could be prepared by the condensation of morphine

(2a) with methyl 3,4,5-tri-0-acetyl-lα-bromo-l-deoxy-d-glucopyranuronate (3) in an aqueous sodium hydroxide-acetone mixture.

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