A novel method for stereoselective glucuronidation

B Fischer, A Nudelman, M Ruse, J Herzig…

Index: Fischer, Bilha; Nudelman, Abraham; Ruse, Margareta; Herzig, Jacob; Gottlieb, Hugo E.; Keinan, Ehud Journal of Organic Chemistry, 1984 , vol. 49, # 25 p. 4988 - 4993

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Citation Number: 73

Abstract

A variety of hydroxylic aglycones can be glucuronidated directly with methyl 2, 3, 4-tri-O- acetylglucopyranuronate (4a), activated with trimethyhilyl trifluoromethanesulfonate (Me3Si- OTf). This reaction provides mostly/3, and sometimes a, glucopyranosiduronic acid derivatives (referred to as glucuronides) rapidly and at low temperatures. The epimeric ratio depends on the relative aglycone nucleophilicity vs. its tendency to form a stabilized ...