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Chinese Journal of Organic Chemistry >

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

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

ARTICLES

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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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

Cite this article

Fakai Zou , Nengzhong Wang , Hui Yao , Hui Wang , Mingguo Liu , Nianyu Huang . Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar[J]. Chinese Journal of Organic Chemistry, 2024 , 44(2) : 593 -604 . DOI: 10.6023/cjoc202307001

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