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

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (9): 1099-1102. Previous Articles Next Articles

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

^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-Hong^a, CHANG Jun-Biao^*,a,b, WANG Qiang^b, QI Xiu-Xiang^c, YU Xue-Jun^c

^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

Abstract

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

Cite this article

DONG Chun-Hong, CHANG Jun-Biao, WANG Qiang, QI Xiu-Xiang, YU Xue-Jun. An Efficient Synthesis of N⁴-Cyclopropylamino-5-fluoro-β-L- uridine from L-Arabinose[J]. Chinese Journal of Organic Chemistry, 2004, 24(9): 1099-1102.

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N⁴-环丙氨-5-氟-β-L-尿苷的合成

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

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N4-环丙氨-5-氟-β-L-尿苷的合成