文献类型：期刊文献

英文题名：Synthesis of 2-(2,3,5-tri-O-benzoyl-D-ribofuranosyl)-1,4-hydroquinone with the catalysis of Lewis acids

作者：He, Li; Xu, Xin; Ren, Zhi-Hua; Zhu, Chen-Jiang; Tang, Yan-Hui; Chen, Guo-Rong

机构：[1]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2006

卷号：26

期号：9

起止页码：1243

外文期刊名：CHINESE JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000240299400010)】；

语种：英文

外文关键词：synthesis; ribofuranoside; Lewis acid; stereoconfiguration

摘要：Reactions of 1,4-dihydroquinone with 1-0-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose in the presence of different Lewis acids afforded alpha- and,beta-aromatic ribofuranosides with good yield, and the stereoconfiguration of 2-(2,3,5-tri-O-benzoyl-D-ribofuranosyl)-1,4-hydroquinone (5) was confirmed by H-1-H-1 NOESY spectrum. Reactions catalyzed by anhydrous AlCl3, ZnCl2 or BF3 center dot Et2O gave beta-O-ribofuranoside 3, whereas TiCl4 afforded a mixture of beta-O-ribofuranoside (3) and alpha- and beta-C-ribofuranosides (5), while SnCl4 produced the alpha- and beta-C-ribofuranosides (5).