Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (1): 138-147.DOI: 10.6023/cjoc201708005 Previous Articles     Next Articles

Special Issue: 庆祝吴养洁院士九十华诞专辑



任行a,b, 陶京朝a, 安浩云b   

  1. a 郑州大学化学与分子工程学院 郑州 450001;
    b 郑州格然林医药科技有限公司 郑州 450016
  • 收稿日期:2017-08-02 修回日期:2017-10-24 发布日期:2017-10-31
  • 通讯作者: 陶京朝
  • 基金资助:


Synthesis of 3'-Azido-D/L-nucleosides

Ren Hanga,b, Tao Jingchaoa, An Haoyunb   

  1. a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001;
    b Zhengzhou Granlen PharmaTech, Ltd., Zhengzhou 450016
  • Received:2017-08-02 Revised:2017-10-24 Published:2017-10-31
  • Contact: 10.6023/cjoc201708005
  • Supported by:

    Project supported by the Key Overseas Chinese Entrepreneurial Team Grant, Awarded by Overseas Chinese Affairs Office of the State Council.

Two orthorganally protected 3'-azido-3'-deoxy-D/L-ribosides were synthesized and successfully glycosylated with various pyrimidine, pyridine and purine related heterocyclic bases. 3'-Azido-3'-deoxy-D-pyrimidine nucleosides, purine nucleosides as well as 3'-azido-3'-deoxy-L-nucleosides were synthesized. 3'-Azido-3'-deoxy-6-azauridine, 4-deoxyuridine, 2-thiouridine, 3-deazauridine, nitropyridinone and isocytidine derivatives were also synthesized as the drug analogues to explore their biological properties. 14 final products are novel and well characterized, while all of the 31 final products were synthesized by the new strategy from the corresponding novel key intermediates. The two key intermediates can be utilized to make all kinds of novel nucleoside derivatives by glycosylating with various heterocyclic bases.

Key words: azido-nucleoside, L-nucleoside, D-nucleoside, synthesis, glycosylation