Studies on the synthesis of estrogen glucosiduronates

• Main Author: Roy, Joan Elaine
• Language: English
• Published: University of British Columbia 2011
• Subjects: Glucosides
• Online Access: http://hdl.handle.net/2429/39791

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. === Medicine, Faculty of === Biochemistry and Molecular Biology, Department of === Graduate