1246814-17-4Relevant articles and documents
Synthesis of kaempferol 3- O -(3″,6″-Di- O - E - p -coumaroyl)-β- D -glucopyranoside, efficient glycosylation of flavonol 3-OH with glycosyl o -alkynylbenzoates as donors
Yang, Weizhun,Sun, Jiansong,Lu, Wenxiang,Li, Yan,Shan, Lei,Han, Wei,Zhang, Wei-Dong,Yu, Biao
experimental part, p. 6879 - 6888 (2010/11/24)
Kaempferol 3-O-(3″,6″-di-O-E-p-coumaroyl)-β-d- glucopyranoside (1), an optimal metabolite of Scots pine seedlings for protection of deep-lying tissue against damaging UV-B, represents a typical acylated flavonol 3-O-glycoside. This compound was synthesized for the first time via two approaches. The first approach, starting with kaempferol, featured formation of the flavonol 3-O-glycosidic linkage with a glycosyl bromide under conventional PTC conditions. In the second approach, 5,7,4′-tri-O-benzyl- kaempferol was readily prepared from 2′,4′,6′- trihydroxyacetophenone and p-hydroxybenzoic acid, which was coupled with a glucopyranosyl o-hexynylbenzoate under the catalysis of a gold(I) complex to provide the desired 3-O-glycoside in excellent yield. A variety of the glycosyl o-hexanylbenzoates equipped with the 2-O-benzoyl group were also proven to be highly efficient donors for construction of the flavonol 3-O-glycosidic linkages.
