Total synthesis of quercetin 3-sophorotrioside

被引：52

作者：

Du, YG ^{[1
]}

Wei, GH

Linhardt, RJ

机构：

[1] Chinese Acad Sci, Res Ctr Ecoenvironm Sci, Beijing 100085, Peoples R China

[2] Rensselaer Polytech Inst, Dept Chem & Chem Biol, Troy, NY 12180 USA

[3] Rensselaer Polytech Inst, Dept Biol, Troy, NY 12180 USA

[4] Rensselaer Polytech Inst, Dept Chem & Biol Engn, Troy, NY 12180 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 06期

关键词：

D O I：

10.1021/jo035722y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5,7-Dihydroxy-3-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-2-(3,4-dihydroxy- phenyl)-4H-1-benzopyran-4-one (quercetin 3-sophorotrioside), a flavonol triglycoside, isolated from Pisum sativurn 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 phasetransfer-catalyzed (PTC) quercetin C-3 glycosylation and silver triflate (AgOTf) promoted carbohydrate chain elongation using both sugar bromide and trichloroacetimidate donors.

引用

页码：2206 / 2209

页数：4

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