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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (9): 989-995. 上一篇    下一篇

研究论文

N-氯苯基-2-脱氧-α-D-吡喃核糖亚胺的合成及其晶体结构

尚培华a 成昌梅*,a 杨 萍a 王如骥b 赵玉芬a

  

  1. (a清华大学化学系 生命有机磷化学及化学生物学教育部重点实验室 北京 100084)
    (b清华大学化学系 北京 100084)

  • 投稿日期:2008-10-29 修回日期:2008-12-10 发布日期:2009-05-14
  • 通讯作者: 成昌梅

Synthesis and Crystral Structure Analysis of N-Chlorophenyl-2-deoxy-α-D-ribopyranosylamine

Shang, Peihua a Cheng, Changmei *,a Yang, Ping a Wang, Ruji b Zhao, Yufen a   

  1. (a Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education),
    Department of Chemistry, Tsinghua University, Beijing 100084)
    (b Department of Chemistry of Tsinghua University, Beijing 100084)
  • Received:2008-10-29 Revised:2008-12-10 Published:2009-05-14
  • Contact: Cheng, Changmei

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在水与甲醇的混合体系中, 2-脱氧-D-核糖与氯代苯胺反应立体选择性地合成了三种N-氯苯基-2-脱氧-α-D-吡喃核糖亚胺(化合物1, 2, 3), 它们的结构经过1H NMR和13C NMR的表征. 将单一构型的N-对氯苯基-2-脱氧-α-D-吡喃核糖亚胺(1)溶于氘代DMSO加入几滴重水, 1H NMR 和13C NMR分析显示1异构化为四种构型的混合物. 培养了化合物1, 2, 3的单晶, 并用X射线衍射法测定了它们的晶体结构. 对晶体结构进行分析, 对反应形成单一构型产物的原因进行了探讨. 并提出了1异构化过程的机理.

关键词: N-氯苯基-2-脱氧-α-D-吡喃核糖亚胺, 立体选择性合成, 构型, 异构化

Three N-chlorophenyl-2-deoxy-α-D-pyranosylamine compounds (1, 2 and 3) were synthesized through a reaction of 2-deoxy-D-ribose with different chlorobenzenamines in water and methanol. Their structures were identified by means of 1H NMR and 13C NMR spectra. Pure N-chlorophenyl-2-deoxy- α-D-ribopyranosylamine was dissolved in d6-DMSO with an additional drop of heavy water at room temperature. It was found that compound 1 isomerized to four configurational isomers, which was confirmed by 1H NMR and 13C NMR analyses. Single crystals of compounds 1, 2 and 3 were grown and their crystal structures were determined by a single crystal diffraction technique. The reason why the reaction gives only a pyranose configuration compound was explained. And the isomerization mechanism of compound 1 was explored.

Key words: N-chlorophenyl-2-deoxy-α-D-ribopyranosylamine, stereoselective synthesis, configuration, isomer