文献类型：期刊文献

英文题名：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

作者：Yang, Weizhun[1,3]; Sun, Jiansong[1]; Lu, Wenxiang[1]; Li, Yan[1]; Shan, Lei[2]; Han, Wei[3]; Zhang, Wei-Dong[2]; Yu, Biao[1]

机构：[1] State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China; [2] Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China; [3] School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China

年份：2010

卷号：75

期号：20

起止页码：6879

外文期刊名：Journal of Organic Chemistry

收录：EI(收录号：20104213303365)

语种：英文

外文关键词：Flavonoids

摘要：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. ? 2010 American Chemical Society.