Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 593-604.DOI: 10.6023/cjoc202307001 Previous Articles     Next Articles



邹发凯, 王能中, 姚辉*(), 王慧, 刘明国, 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 发布日期:2023-10-23
  • 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)

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

Fakai Zou, Nengzhong Wang, Hui Yao(), Hui Wang, Mingguo Liu, Nianyu Huang()   

  1. 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
  • Received:2023-07-01 Revised:2023-09-26 Published:2023-10-23
  • Contact: E-mail:;
  • 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)

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