Glucuronidation of Two Novel Metabolites of Benproperine with Trichloroacetimidate Donor

【Abstract】 The glucuronide metabolites of benproperine were synthesized from mono-hydroxylate metabolites of benproperine that were treated with methyl(2,3,4-tri-O-acetyl-1-O-trichloroacetimidoyl)-α-D-glucopyranuronate with BF_ 3 ·Et_ 2 O as the promoter followed by basic hydrolyzation with Na_ 2 CO_ 3 . The form of basic acceptors, the order of addition, and the promoter are all important variables in this glucuronidation. The salt form of the basic acceptor was found to be better than its free form for glucuronidation with a Lewis acid as the promoter. Two mono-hydroxylated benproperines were synthesized from 2-benzylphenol in three steps.更多还原