N-氯苯基-2-脱氧-α-D-吡喃核糖亚胺的合成及其晶体结构  

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

作　　者：尚培华[1] 成昌梅[1] 杨萍[1] 王如骥[2] 赵玉芬[1] 

机构地区：[1]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 [2]清华大学化学系,北京100084

出　　处：《化学学报》2009年第9期989-995,共7页Acta Chimica Sinica

基　　金：国家自然科学基金(No.20132020)资助项目

摘　　要：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1HNMR和13CNMR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,1HNMR和13CNMR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.Three N-chlorophenyl-2-deoxy-a-D-pyranosylamine compounds （1, 2 and 3） were syntheslzed 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.

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 

分 类 号：O626[理学—有机化学]