Synthesis of morphine-3-glucuronide
Berrang, B., Twine, C., Hennessee, G. R., & Carroll, F. (1975). Synthesis of morphine-3-glucuronide. Synthetic Communications, 5(3), 231-236. DOI: 10.1080/00397917508064116
Morphine-3-glucuronide [1, morphine-(3?-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-l?-bromo-l-deoxy-d-glucopyranuronate (3) in an aqueous sodium hydroxide-acetone mixture.