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

机构：[1]Second Mil Med Univ, Sch Pharm, Dept Phyiochem, Shanghai 200433, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bio Organ & Nat Produers Chem, Shanghai 200032, Peoples R China;[3]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R 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：;WOS:【SCI-EXPANDED(收录号:WOS:000282604900016)，CCR-EXPANDED(收录号:WOS:000282604900016)】；

语种：英文

摘要：Kaempferol 3-O-(3 '',6 ''-di-O-E-p-coumaroyl)-beta-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 km the first time via two approaches The first approach starting with kaempterol. featured formation or the flavonol 3-O-glycosidic linkage with a glycosyl biomide under conventional PTC conditions In the second approach. 5.7 4'-tri-O-benzyl-kampferol was readily prepared from oxyacetophenone 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 C also pi oven to he highly efficient donors for construction of the flavonol 3-O-glycosidic linkages