Synthesis of methyl (allyl 2,3-di-O-benzyl-β-d-galactopyranosid)uronate and methyl (2,3-di-O-benzyl-α- and β-d-galactopyranosyl fluoride)uronate
1988; Elsevier BV; Volume: 173; Issue: 2 Linguagem: Inglês
10.1016/s0008-6215(00)90828-0
ISSN1873-426X
AutoresYoshiaki Nakahara, Tomoya Ogawa,
Tópico(s)Phytochemical Studies and Bioactivities
ResumoThe glucuronide metabolites of benproperine were synthesized from mono-hydroxylate metabolites of benproperine that were treated with methyl(2,3,4-tri-O-acetyl-l-O-trichloroacetimidoyl)-α-D-glucopyranurone with BF3 · Et2O as the promoter followed by basic hydrolyzation with Na2CO3. 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.
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