Total synthesis of quercetin 3-sophorotrioside

J Org Chem. 2004 Mar 19;69(6):2206-9. doi: 10.1021/jo035722y.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbohydrate Conformation
  • Glucans / chemical synthesis*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosylation
  • Pisum sativum / chemistry*
  • Quercetin / analogs & derivatives*
  • Quercetin / chemical synthesis*
  • Stereoisomerism

Substances

  • Glucans
  • Glycosides
  • quercetin 3-sophorotrioside
  • Quercetin
  • sophorose