A facile synthesis of isoflavone 7-O-glucuronides

An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isoflavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis.