廉价钴催化下β-D-葡萄烯糖硫苷的立体选择性合成  

Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides

作　　者：华敏 孙阳星 张雪晴 姚辉 黄年玉 Hua Min;Sun Yangxing;Zhang Xueqing;Yao Hui;Huang Nianyu(Hubei Key Laboratory of Natural Products Research and Development,College of Biological and Pharmaceutical Sciences,China Three Gorges University,Yichang,Hubei 443002)

机构地区：[1]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室,湖北宜昌443002

出　　处：《有机化学》2022年第7期2140-2154,共15页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.82003621);湖北省自然科学基金(2020CFB205);湖北省教育厅自然科学基金(No.Q20201204)资助项目。

摘　　要：报道了以葡萄烯糖-3-吡啶酸酯和硫酚/硫醇为原料,Co(BF_(4))_(2)催化下立体选择性合成β-D-葡萄烯糖硫苷的方法.目标化合物的化学结构经过了核磁共振、高分辨质谱和单晶X射线衍射的确证.该反应对各类硫醇和硫酚具有良好的官能团兼容性,能耐受含酯基、酚/醇羟基、氨基和乙酰氨基等活性硫亲核试剂,还可用于硫糖肽的高效合成,为硫糖苷的快速制备提供了新方案.A method of stereoselective synthesis of β-D-thioglycosides from glucosyl-3-pyridinate donor and thiophenols/thiols catalyzed by Co(BF_(4))_(2) was reported.The chemical structures of the target compounds were confirmed by nuclear magnetic resonance,high-resolution mass spectrometry and single crystal X-ray diffraction.The reaction has good functional group compatibility with all kinds of mercaptans and thiophenols,and can tolerate active sulfur nucleophiles including ester group,phenol/alcohol hydroxyl group,amino group and acetylamino group.It can also be used for the efficient synthesis of thioglycopeptides,which provides a new way for the rapid preparation of thioglycosides.

关 键 词：CO催化 糖基化反应 硫糖苷 糖肽 合成 

分 类 号：O629.13[理学—有机化学]