有机化学 ›› 2022, Vol. 42 ›› Issue (7): 2140-2154.DOI: 10.6023/cjoc202202021 上一篇    下一篇

研究论文

廉价钴催化下β-D-葡萄烯糖硫苷的立体选择性合成

华敏, 孙阳星, 张雪晴, 姚辉*(), 黄年玉*()   

  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
  • 收稿日期:2022-02-18 修回日期:2022-03-23 发布日期:2022-08-09
  • 通讯作者: 姚辉, 黄年玉
  • 基金资助:
    国家自然科学基金(82003621); 湖北省自然科学基金(2020CFB205); 湖北省教育厅自然科学基金(Q20201204)

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

Min Hua, Yangxing Sun, Xueqing Zhang, Hui Yao(), Nianyu Huang()   

  1. Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002
  • Received:2022-02-18 Revised:2022-03-23 Published:2022-08-09
  • Contact: Hui Yao, Nianyu Huang
  • Supported by:
    National Natural Science Foundation of China(82003621); Natural Science Foundation of Hubei Province(2020CFB205); Natural Science Foundation of the Educational Commission of Hubei Province(Q20201204)

报道了以葡萄烯糖-3-吡啶酸酯和硫酚/硫醇为原料, Co(BF4)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.

关键词: Co催化, 糖基化反应, 硫糖苷, 糖肽, 合成

A method of stereoselective synthesis of β-D-thioglycosides from glucosyl-3-pyridinate donor and thiophenols/ thiols catalyzed by Co(BF4)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.

Key words: Co-catalysis, glycosylation reaction, thioglycoside, glycopeptide, synthesis