Total synthesis of quercetin 3-sophorotrioside.
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.
Du
Yuguo
Y
Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, 100085 Beijing, China. ygdu2001j@yahoo.com
Wei
Guohua
G
Linhardt
Robert J
RJ
D002236:Carbohydrate Conformation; D005936:Glucans / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D018532:Pisum sativum / Q000737:chemistry*; D011794:Quercetin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D005936:Glucans; D006027:Glycosides; C485516:quercetin 3-sophorotrioside; D011794:Quercetin; C003328:sophorose