二苯乙烯C-糖苷的立体选择性合成  

Stereoselective Synthesis of Stilbene C-Glucosides

作　　者：马文晋 刘海平 雷田 邱海平 袁嘉遥 李文玲 Ma Wenjin;Liu Haiping;Lei Tian;Qiu Haiping;Yuan Jiayao;Li Wenling(School of Chemistry and Chemical Engineering,Lanzhou Jiaotong University,Lanzhou 730070)

机构地区：[1]兰州交通大学化学化工学院,兰州730070

出　　处：《有机化学》2024年第9期2943-2949,共7页Chinese Journal of Organic Chemistry

基　　金：甘肃省自然科学基金(No. 22JR5RA347)资助项目.

摘　　要：采用不同保护基的二苯乙烯单体与乙酰化糖供体在BF_(3)·OEt_(2)催化下进行C-糖苷化反应,分别立体选择性地合成了相应的C-糖苷化产物,二苯乙烯上保护基的类型直接影响10-C-β-糖苷化产物和12-C-β-糖苷化产物的产率.二苯乙烯糖苷中间体上多个保护基的完全脱除虽未成功,但选择性脱除糖苷上苄基保护基得到的溴代白藜芦醇10-C-β-糖苷类似物确证了C-糖苷化反应产物的结构.The C-glycosylation reactions of different protected stilbene monomers with anomeric acetylated glucosyl donor were promoted by BF_(3)·OEt_(2),and their corresponding aryl C-glucosides were stereoselectively synthesized.The kind and stablity of phenolic protecting groups in stilbenes directly influenced the product yields of 10-C-β-glucosides and 12-C-β-glucosides.Final global deprotection of stilbene C-glucoside intermediates was unsuccessful,but the structures of 10-C-β-glucoside product were confirmed by the selective debenzylation of brominated resveratrol 10-C-β-glucoside analogue.

关 键 词：白藜芦醇C-糖苷 二苯乙烯 芳基C-糖苷化 保护基 合成 

分 类 号：O629.13[理学—有机化学]