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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (9): 1099-1102. 上一篇    下一篇

研究简报

N4-环丙氨-5-氟-β-L-尿苷的合成

董春红a, 常俊标*,a,b, 王强b, 祁秀香c, 余学军c   

  1. a中国科学技术大学化学系 合肥 230026;
    b河南省科学院质检研究中心 郑州 450002;
    c中国科学院兰州化学物理研究所 兰州 730000
  • 收稿日期:2003-11-25 修回日期:2004-02-06 接受日期:2004-03-25 发布日期:2022-09-20
  • 基金资助:
    国家自然科学基金(No. 29972009)、国家自然科学基金主任基金(No. 20342005)、河南省杰出青年基金资助项目.

An Efficient Synthesis of N4-Cyclopropylamino-5-fluoro-β-L- uridine from L-Arabinose

DONG Chun-Honga, CHANG Jun-Biao*,a,b, WANG Qiangb, QI Xiu-Xiangc, YU Xue-Junc   

  1. aDepartment of Chemistry, University of Science and Technology of China,Hefei 230026;
    bResearch Center of Henan Academy, Zhengzhou 450002;
    cLanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
  • Received:2003-11-25 Revised:2004-02-06 Accepted:2004-03-25 Published:2022-09-20
  • Contact: * E-mail: jbchang@public2.zz.ha.cn

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报道了N4-环丙氨-5-氟-β-L-尿苷的合成新方法,以L-阿拉伯糖为起始原料合成了化合物L-吡喃核糖(6),然后经三步反应合成了重要中间体1-氧-乙酰基-2,3,5-三-氧-苯甲酰基-β-L-呋喃核糖(9),与硅烷化的5-氟尿嘧啶缩合得到了带有保护基的5-氟-β-L-尿苷(10),脱保护后与六甲基二硅氮烷(HMDS)、环丙氨、硫酸铵(催化剂)一锅反应得到了目标化合物N4-环丙氨-5-氟-β-L-尿苷(12).产物结构经MS,UV, IR, NMR,元素分析等确认.

关键词: L-阿拉伯糖, 合成, L-核苷

An efficient synthesis of N4-cyclopropylamino-5-fluoro-β-L-uridine was developed from L-arabinose. L-Arabinose was converted to compound L-ribopyranose (6), which was used for the synthesis of the key intermediate 2,3,5-tri-O-benzoyl-1-O-acetyl-β-L-ribofuranose (9).The compound 9 was subjected to condensation with silylated 5-fluoro-uracil to give the resulting protected compound 5-fluoro-3-(2',3',5'-tri-O-benzoyl-β-L-ribofuranosyl)-uracel(10). Compound 10 was deprotected to give 5-fluoro-β-L-uridine (11). One-pot reaction of compound 11, HMDS (1,1,1,3,3,3-Hexamethyldisilazane), (NH4)2SO4 and cyclopropylamine was carried out to get N4-cyclopropylamino-5-fluoro-β-L-uridine. Thestructures of these products were identified by the MS, UV, IR, NMR, elemental analysis and X-ray crystallographic analysis.

Key words: L-arabinose, synthesis, L-nucleoside