Total Synthesis of Quercetin 3-Sophorotrioside
- 25 February 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (6), 2206-2209
- https://doi.org/10.1021/jo035722y
Abstract
5,7-Dihydroxy-3-[β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-β-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.Keywords
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