开放体系中芳基岩藻糖/阿拉伯糖碳苷的立体选择性合成
收稿日期: 2022-02-04
修回日期: 2022-02-23
网络出版日期: 2022-03-22
基金资助
高等学校学科创新引智计划(111 Project); 高等学校学科创新引智计划(D20015); 湖北省自然科学基金(2020CFB205); 湖北省教育厅(Q20201204); 三峡大学学位论文培优基金(2021SSPY158)
Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides
Received date: 2022-02-04
Revised date: 2022-02-23
Online published: 2022-03-22
Supported by
Programme of Introducing Talents of Discipline to Universities(111 Project); Programme of Introducing Talents of Discipline to Universities(D20015); Natural Science Foundation of Hubei Province(2020CFB205); Educational Commission of Hubei Province(Q20201204); Dissertation Training Fund of China Three Gorges University(2021SSPY158)
报道了3,4-O-碳酸酯烯糖和芳基硼酸在二乙酸-1,2-双(苯亚磺酰)乙基钯(II) (White催化剂)催化下, 经脱羧烯丙基化反应在开放条件下立体选择性合成岩藻糖和阿拉伯糖碳苷的方法. 产物的立体构型经NMR、HRMS和X射线单晶衍射等技术确定. 该方法具有良好的官能团兼容性, 竞争性反应表明反应可耐受氨基、醇羟基和酚羟基. 产物的进一步官能团化可用于制备各类碳糖苷. 该方法条件温和, 操作简单, 底物应用范围广, 为碳苷化合物库的快速构建提供了新思路.
关键词： 3,4-O-碳酸酯烯糖; 立体选择性; 岩藻糖碳苷; 阿拉伯糖碳苷; 碳糖苷化反应
来梦楠 , 王秋圆 , 华敏 , 黄年玉 , 姚辉 . 开放体系中芳基岩藻糖/阿拉伯糖碳苷的立体选择性合成[J]. 有机化学, 2022 , 42(6) : 1694 -1705 . DOI: 10.6023/cjoc202202002
An open-air stereoselective preparation of C-aryl fucosides and arabinosides was reported using 3,4-O-carbonate glycals and arylboronicic acids based on a palladium-catalyzed decarboxylative allylation at ambient conditions and the configurations of products were determined by NMR, HRMS and X-ray single crystal diffraction analysis. Competitive reactions indicated that this approach has good compatibility with amino and alcoholic/phenolic hydroxyl groups. Further functionlization of unsaturated C-glycosides can be used to prepare a variety of C-glycosides. This mild method is simple in operation, wide application in substrate range, which provides a new idea for the rapid construction of carbohydrate library.
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