有机化学 ›› 1999, Vol. 19 ›› Issue (6): 625-629. 上一篇    下一篇

研究论文

在多糖衍生物类色谱柱上手性拆分β-氨基醇及β-羟基 硫醚类化合物

夏立钧;吴Jie;唐民华;侯雪龙;戴立信   

  1. 中国科学院上海有机化学研究所.上海(200032)
  • 发布日期:1999-12-25

Direct enantiomeric separation of β-aminoalcohols and β-hydroxy sulfides using polysaccharide derivatives as chiral stationary phases

Xia Lijun;WU Jie;Tang Minhua;Hou Xuelong;Dai Lixin   

  1. Shanghai Inst Organ Chem., CAS.Shanghai(200032)
  • Published:1999-12-25

在以正己烷-异丙醇为移动相的体系中,用ChiralcelOD,ChiralcelOJ及ChiralpakAD作为手性固定相对13种β-氨基醇及β-羟基硫醚类化合物对映体进行HPLC手性拆分,这些化合物至少能在一支柱上得到基线级分离。考察了它们于不同浓度配比的这类洗脱体系中在柱上的色谱行为。实验表明化合物取代基的性质明显影响它们在手性柱上的拆分。手性固定相与外消旋样品上的极性基团之间的氢键作用和π-π作用可能是进行手性识别的主要原因。方法已用于非手性环氧化合物不对称开环反应产物β-氨基醇及β-羟基硫醚类化合物的光学纯度鉴定。

关键词: 硫醚P, 高效液体色谱, 消旋体拆分, 手性固定相, β-取代基, 氨基醇P

Direct enantiomeric separation of racemic mixtures of 13 β-amino alcohols and β-hydroxy sulfides was achieved by HPLC using Chiralcel OD, Chiralcel OJ and Chiralpak AD as chiral stationary phases and hexane/2-propanol mixture as eluent. These racemates were completely separated into enantiomers at least on one of these stationary phases. The chromatographic parameters of these racemates on AD, OD and OJ columns at various ratios of hexane/2-propanol were examined. The results showed that the properties of substituents of the compounds obviously had effects on their resolution on columns. The hydrogen bonding and π-π interactions between the chiral stationary phase and the polar group of racemates may be responsible for the chiral recognition. This method had been applied to determination of the optical purity of the product from asymmetric ring opening of meso- epoxides.

Key words: SULFUR ETHER P, MESOTOMY, HIGH-SPEED LIQUID CHROMATOGRAPHY, AMINO ALCOHOL P

中图分类号: