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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (10): 1394-1397. 上一篇    下一篇

研究论文

9-(β-D-2'-脱氧核糖基)-6-甲基嘌呤的合成

李庶心*,a，江发龙a,b，赵砚瑾a，郭金华a，王志清a   

  1. (a军事医学科学院放射与辐射医学研究所 北京 100850)
    (b江西中医学院 南昌 330006)
  • 收稿日期:2005-09-21 修回日期:2006-02-21 发布日期:2006-09-19
  • 通讯作者: 李庶心

An Efficient Synthesis of 9-β-D-2'-Deoxyribofuranosyl-6-methylpurine

LI Shu-Xin*,a,JIANG Fa-Longa,b,ZHAO Yan-Jina
GUO Jin-Huaa,WANG Zhi-Qinga   

  1. (a Institute of Radiation and Irradiation Medicine, Academy of Military Medical Science, Bei-jing 100850)
    (b Jiangxi Traditional Chinese Medicine of Institute, Nanchang 330006)
  • Received:2005-09-21 Revised:2006-02-21 Published:2006-09-19
  • Contact: LI Shu-Xin

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报道了9-(β-D-2'-脱氧核糖基)-6-甲基嘌呤合成的新方法. 以肌苷1为原料, 经酯化、氯化、氨解得6-氯嘌呤核苷(4), 再经过羟基保护、6-位甲基化反应及脱保护反应得到关键中间体6-甲基嘌呤核苷7, 用1,3-二氯-1,1,3,3-四异丙基二硅氧烷保护7核糖上的3,5-二羟基, 2-羟基与苯氧基硫代甲酰氯反应后得到9, 然后与氢化三正丁基锡[HSn(Bu-n)3]还原脱氧, 最后脱保护得到目标化合物11. 产物结构经MS, 1H NMR, 元素分析等鉴定.

关键词: 核苷, 呤核苷, 合成

A new method for preparing 9-β-D-2'-deoxyribofuranosyl-6-methylpurine from inosne (1) is described. Inosne was converted to 6-chlorolpurinenucleoside (4) via esteriflcation, chlorination and deacetylation, then through protecting, deacetylation and deprotecting reactions to give the key intermediate 6-methylpurinenucleoside (7). The compound 7 was protected with O[Si(i-Pr)2Cl]2 and reacted with phenyl carbonochloridothioate to give compound 9. The compound 9 was converted to target compound 11 by reduction and deprotecting reaction. The structures of these products were identified by MS, 1H NMR spectra and elemental analysis.

Key words: purinenucleoside, synthesis, nucleoside