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2024 , Vol. 44 >Issue 2: 593 - 604

DOI: https://doi.org/10.6023/cjoc202307001

研究论文

1β-/3R-芳基硫代糖的区域与立体选择性合成

  • 邹发凯 ,
  • 王能中 ,
  • 姚辉 ,
  • 王慧 ,
  • 刘明国 ,
  • 黄年玉
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  • 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中国轻工业功能酵母重点实验室 湖北宜昌 443002

收稿日期: 2023-07-01

  修回日期: 2023-09-26

  网络出版日期: 2023-10-26

基金资助

国家自然科学基金(22207063); 高等学校学科创新引智计划(111 计划, No. D20015); 湖北省自然科学基金(2022CFB838); 及湖北省教育厅(D20221204); 及湖北省教育厅(Q20221212)

收起

Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar

  • Fakai Zou ,
  • Nengzhong Wang ,
  • Hui Yao ,
  • Hui Wang ,
  • Mingguo Liu ,
  • Nianyu Huang
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  • Hubei 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
* Corresponding authors. E-mail: ;

Received date: 2023-07-01

  Revised date: 2023-09-26

  Online published: 2023-10-26

Supported by

National Natural Science Foundation of China(22207063); Programme of Introducing Talent of Discipline to Universities(No. D20015); Natural Science Foundation of Hubei Province(2022CFB838); Educational Commission of Hubei Province(D20221204); Educational Commission of Hubei Province(Q20221212)

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摘要

硫代糖因具有优良的生物活性在生物医药领域备受关注, 化学合成是得到硫代糖的重要途径. 采用6-膦酸酯- 3,4-碳酸酯半乳烯糖和硫酚为原料, 分别以Pd2(dba)3和NiBr2为催化剂调控了1β-芳基硫代糖和(3R)-芳基硫代糖的区域和立体选择性合成. 目标化合物的结构通过核磁共振、高分辨质谱和单晶X射线衍射进行了表征. 该合成方法对各类官能团取代的硫酚都有良好的兼容性, 可用于活性天然产物的硫糖基化修饰, 为1β-/(3R)-芳基硫代糖化合物库的快速构建和药物发现提供了新方法.

关键词： Pd催化; Ni催化; D-半乳糖; 硫代糖; 合成

本文引用格式

邹发凯 , 王能中 , 姚辉 , 王慧 , 刘明国 , 黄年玉 . 1β-/3R-芳基硫代糖的区域与立体选择性合成[J]. 有机化学, 2024 , 44(2) : 593 -604 . DOI: 10.6023/cjoc202307001

Abstract

Thiosugars have attracted much attention in the field of pharmaceuticals because of their excellent biological activities, and chemical synthesis is an important way to obtain thiosugars. Using 6-O-diphenylphosphoryl-3,4-O-carbonate-D-gala- ctal and thiophenols as starting materials, the regio- and stereo-selective syntheses of 1β-/(3R)-aryl thiosugars were controlled with NiBr2 and Pd2(dba)3 catalysts, respectively. The structures of the target compounds were characterized by nuclear magnetic resonance, high-resolution mass spectrometry and single crystal X-ray diffraction. This method exhibited favourable compatibility with various functional groups substituted thiophenols, which could be used for the structural modification of active natural products. The research work is help for the rapid construction of the compound library of 1β-/(3R)-aryl thiosugars for drug discovery.

Key words： Pd catalysis; Ni catalysis; D-galactal; thiosugar; synthesis

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