Total Synthesis of Quercetin 3-Sophorotrioside

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Authors
Du, Yuguo
Wei, Guohua
Linhardt, Robert J.
Issue Date
2004-03-19
Type
Article
Language
ENG
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Abstract
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.
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Journal of Organic Chemistry, 69, 2206-2209
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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.
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223263
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