Total Synthesis of Quercetin 3-Sophorotrioside

Du, Yuguo
Wei, Guohua
Linhardt, Robert J.
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Total Synthesis of Quercetin 3-Sophorotrioside, Y. Du, G. Wei, R. J. Linhardt, Journal of Organic Chemistry, 69, 2206-2209, 2004.
5,7-dihydroxy-3-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one (quercetin 3-sophorotrioside), a flavonol triglycoside, isolated from Pisum sativum shoots and showing protective effects on liver injury induced by chemicals, was synthesized for the first time. The target compound was successfully synthesized in eight linear steps and in 39% overall yield through a combination of phase-transfer-catalyzed (PTC) quercetin C-3 glycosylation and silver triflate (AgOTf) promoted carbohydrate chain elongation using both sugar bromide and trichloroacetimidate donors.
Journal of Organic Chemistry, 69, 2206-2209
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The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Journal of Organic Chemistry