有机化学 ›› 2024, Vol. 44 ›› Issue (9): 2943-2949.DOI: 10.6023/cjoc202402001 上一篇    下一篇

研究简报

二苯乙烯C-糖苷的立体选择性合成

马文晋, 刘海平, 雷田, 邱海平, 袁嘉遥, 李文玲*()   

  1. 兰州交通大学化学化工学院 兰州 730070
  • 收稿日期:2024-04-02 修回日期:2024-04-23 发布日期:2024-05-10
  • 通讯作者: 李文玲
  • 基金资助:
    甘肃省自然科学基金(22JR5RA347)

Stereoselective Synthesis of Stilbene C-Glucosides

Wenjin Ma, Haiping Liu, Tian Lei, Haiping Qiu, Jiayao Yuan, Wenling Li()   

  1. School of Chemistry and Chemical Engineering, Lanzhou Jiaotong University, Lanzhou 730070
  • Received:2024-04-02 Revised:2024-04-23 Published:2024-05-10
  • Contact: Wenling Li
  • Supported by:
    Natural Science Foundation of Gansu Province(22JR5RA347)

采用不同保护基的二苯乙烯单体与乙酰化糖供体在BF3•OEt2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.

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

The C-glycosylation reactions of different protected stilbene monomers with anomeric acetylated glucosyl donor were promoted by BF3•OEt2, 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.

Key words: resveratrol C-glucoside, stilbene, aryl C-glycosylation, protecting groups, synthesis