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Studies on the synthesis of estrogen glucosiduronates

University of British Columbia

An investigation of the reactions involved in the chemical synthesis of estrogen glucosiduronates was undertaken to establish conditions for the synthesis of the doubly labeled conjugates. The α- and β-anomers of methyl 1,2,3,4-tetra-0-acetyl-D-glucuronate were prepared from glucuronolactone by base and acid catalyzed acetylations respectively. Bromination of either of these compounds yielded methyl 2,3,4-tri-0-acetyl-1-bromo-1-deoxy-α-D-glucuronate. Estrone was converted by a series of reactions to 3,16α-diacetoxy-17-keto-estra-1,3,5(10)-triene. Attempted reduction of the 17-keto group was unsuccessful, and for this reason estriol-17β-glucosiduronate could not be prepared. Estradiol glucosiduronates could not be obtained in crystalline form in significant yields. Estrone was successfully conjugated with methyl 2,3,4-tri-0-acetyl-1-bromo-1-deoxy-α-D-glucuronate. Deacetylation under alkaline conditions gave a solid compound presumed to be estrone glucosiduronate.

Text

2011-12-20

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http://hdl.handle.net/2429/39791

Biochemistry and Molecular Biology

University of British Columbia

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