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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (03): 431-435. 上一篇    下一篇

研究简报

核苷类似物5-杂环取代或1,5-二杂环取代-1-α/β-D-5-脱氧呋喃核糖的合成

姚颖a，罗有福a，黄文才a，李子成*,a,b，陈淑华b   

  1. (a四川大学化工学院 成都 610065)
    (b四川大学化学学院 成都 610064)
  • 收稿日期:2008-12-29 修回日期:2009-06-18 发布日期:2010-03-28
  • 通讯作者: 李子成 E-mail:sculzc@scu.edu.cn

Synthesis of Nucleoside Analogs 5-Heterocyclo or 1,5-Diheterocyclo-1-α/β-D-5-deoxyribofuranoses

Yao Yinga,Luo Youfua,Huang Wencaia,Li Zicheng*,a,b,Chen Shuhuab   

  1. (a School of Chemical Engineering, Sichuan University, Chengdu 610065)
    (b Faculty of Chemistry, Sichuan University, Chengdu 610064)
  • Received:2008-12-29 Revised:2009-06-18 Published:2010-03-28
  • Contact: LI Zi-Cheng E-mail:sculzc@scu.edu.cn

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核糖在酸的作用下于甲醇中闭环得到呋喃核糖甲苷, 将其2,3-二羟基形成异亚丙基后, 与对甲苯磺酰氯作用生成5-O-对甲苯磺酰基-2,3-O-异亚丙基-1-α/β-D-呋喃核糖甲苷, 最后与取代哌嗪或吗啉反应, 再在酸的作用下除去2,3-保护基, 得到5-脱氧-5-杂环取代-1-α/β-D-呋喃核糖甲苷. 它们的结构经1H NMR和MS确证.

关键词: 核苷类似物, 5-(4-取代哌嗪-1-基)呋喃核糖甲苷, 5-脱氧-1,5-二杂环取代呋喃核糖, 合成

D-Ribose was cyclized to ribofuranose in methanol under acid condition. After protection of the 2- and 3-hydroxy groups by isopropylene, the sugar was reacted with p-toluenesulfonyl chloride to afford 5-O-p-toluenesulfonyl-2,3-O-isopropylene-1-α/β-D-ribofuranose, whose toluenesulfonyloxy group was replaced by N-substituted piperazine or morpholine, and the isopropylene group was removed under acid condition to give 5-heterocyclo-1-α/β-D-5-deoxyribofuranoses. The target compounds were identified by 1H NMR, MS techniques and element analysis.

Key words: nucleoside analog, 5-(4-substituted-piperazinyl)ribofuranose, 1,5-bis-heterocyclo-5-deoxyribofuranoside, synthesis