Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides

doi:10.6023/cjoc202202002

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1694-1705.DOI: 10.6023/cjoc202202002 Previous Articles Next Articles

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开放体系中芳基岩藻糖/阿拉伯糖碳苷的立体选择性合成

来梦楠, 王秋圆, 华敏, 黄年玉^*(), 姚辉^*()

三峡大学生物与制药学院天然产物研究与利用湖北省重点实验国轻工业功能酵母重点实验室湖北宜昌 443002

收稿日期:2022-02-04 修回日期:2022-02-23 发布日期:2022-03-21
通讯作者: 黄年玉, 姚辉
作者简介:
† 共同第一作者
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

Mengnan Lai, Qiuyuan Wang, Min Hua, Nianyu Huang(), Hui Yao()

Key Laboratory of Natural Products Research and Development, Key Laboratory of Functional Yeast (China National Light Industry), College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002

Received:2022-02-04 Revised:2022-02-23 Published:2022-03-21
Contact: Nianyu Huang, Hui Yao
About author:
† These authors contributed equally to this work
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)

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Abstract

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.

Key words: 3,4-O-carbonate glycal, stereoselectivity, C-fucoside, C-arabinoside, C-glycosylation

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Mengnan Lai, Qiuyuan Wang, Min Hua, Nianyu Huang, Hui Yao. Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1694-1705.

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开放体系中芳基岩藻糖/阿拉伯糖碳苷的立体选择性合成

Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides

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