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

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.