Total Synthesis of Quercetin 3-Sophorotrioside | Zendy

Yuguo Du | Zendy; Guohua Wei | Zendy; Robert J. Linhardt | Zendy

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Total Synthesis of Quercetin 3-Sophorotrioside

Author(s) -

Yuguo Du,

Guohua Wei,

Robert J. Linhardt

Publication year - 2004

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo035722y

Subject(s) - pisum , sativum , quercetin , glycosylation , chemistry , glycoside , yield (engineering) , sugar , stereochemistry , biochemistry , botany , biology , antioxidant , materials science , metallurgy

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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