高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (8): 1427.

• 研究简报 • 上一篇    下一篇

一锅法合成O-(3-薯蓣甙元)-O′-[5′-(3′-叠氮-3′-脱氧胸苷)]-氢亚磷酸酯

肖强1, 巨勇1,2, 赵玉芬1   

  1. 1. 清华大学生命科学与工程学院化学系, 生命有机磷教育部重点实验室, 北京 100084;
    2. 兰州大学应用有机化学国家重点实验室, 兰州 730000
  • 收稿日期:2002-08-07 出版日期:2003-08-24 发布日期:2003-08-24
  • 通讯作者: 巨勇(1961年出生),男,博士,副教授,从事化学生物学研究.E-mail:juyong@tsinghua.edu.cn E-mail:juyong@tsinghua.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:20132020,20172033);京港三校中医药合作计划《创意小课题》基金;清华大学基础研究基金(批准号:JC2002046)资助

One-pot Synthesis of the O-(3-Diosgenin) O′-[5′-(3′-Azido- 3′-deoxythymidine)]-H-phosphonate

XIAO Qiang1, JU Yong1,2, ZHAO Yu-Fen1   

  1. 1. Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing 100084, China;
    2. National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2002-08-07 Online:2003-08-24 Published:2003-08-24

关键词: 薯蓣甙元, 3&prime, -叠氮-3&prime, -脱氧胸苷, 转酯化反应, 氢亚磷酸酯, 磷酰化

Abstract: Azido-3′-deoxythymidine(AZT) was the first clinically approved drug against HIVinfection, despite its undesirable side reactions, such as bone marrow suppression.In our aim to develop new chemical entity of anti-tumor and anti-HIV, the H-phosphonate 6 of AZTconjugate with diosgenin was synthesized by a tandem transesterification reaction for the first time.There are the merits of easy operation and high yield in the reported method.It could be extended to synthesize other diosgenin phosphonate conjugates such as carbohydrate and peptide.

Key words: Diosgenin, 3′-Azido-3′-deoxythymidine(AZT), Transesterification, H-Phosphonate, Phosphorylation

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