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

doi:10.6023/cjoc201708005

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

Articles

3'-叠氮D/L-核苷的合成

任行^a,b, 陶京朝^a, 安浩云^b

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 E-mail:han@granlen.com
基金资助:
国务院重点华侨华人创业团队经费资助项目.

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

Ren Hang^a,b, Tao Jingchao^a, An Haoyun^b

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 E-mail:han@granlen.com
Supported by:
Project supported by the Key Overseas Chinese Entrepreneurial Team Grant, Awarded by Overseas Chinese Affairs Office of the State Council.

1. Synthesis of 3'-Azido-D/L-nucleosides.PDF(1946KB)

Abstract

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

Cite this article

Ren Hang, Tao Jingchao, An Haoyun. Synthesis of 3'-Azido-D/L-nucleosides[J]. Chin. J. Org. Chem., 2018, 38(1): 138-147.

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3'-叠氮D/L-核苷的合成

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

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