三(3,5-二甲基苯基氨基甲酸酯)多糖手性固定相拆分芳基硒代甘油醚对映体

Enantioseparation of 1-substituted 3-arylseleno-2-propanols onPolysaccharide Tris(3,5-dimethylphenylcarbamate)Chiral Stationary Phases

采用Chiralcel OD H和Chiralpak AD H手性柱,研究5种新近合成的外消旋双芳基硒代甘油硫醚和 4 种芳基硒代甘油烷氧醚对映体的高效液相色谱拆分方法.对比这两种手性固定相、异丙醇和乙醇流动相调节剂、以及样品结构对硒代甘油醚色谱拆分的影响.除样品(1c)外,其他8个外消旋硒代甘油醚样品均可达到基线拆分.

The enantiomer separation of nine pairs of racemic 1-arylthio-3-arylseleno -2-propanols and 1-alkoxy-3-arylseleno-2-propanols was achieved with high performance liquid chromatography by using cellulose tris(3,5-dimethylphenyl carbamate) (Chiralcel OD-H) and amylose tris(3,5-dimethylphenylcarbamate) (Chiralpak AD-H) as chiral stationary phases and hexane-2-propanol or hexane-ethanol as mobile phases in various percentages.Amylose tris(3,5-dimethylphenylcarbamate) exhibited higher chiral recognition ability compared to cellulose tris(3,5-dimethylphenylcarbamate).The effects of alcohol in the mobile phase and solute structures on the retention and resolution were investigated.On the Chiralcel OD-H column,solutes elute faster with ethanol than with 2-propanol modifier as expected from the higher polarity of ethanol. However,on Chiralpak AD-H column the retention factors of all the enatiomers increase,the enantioseparation factors and resolutions dramatically change on changing 2-propanol to ethanol.The explanation may be that ethanol changes the higher order structure of amylose.The enantioseparation on the Chiralpak AD-H column is much more influenced by the kind of alcohol in the mobile phase than the Chiralcel OD-H.Under optimized conditions,baseline enantioseparation of eight pairs of racemic 1-substituted 3-arylseleno-2-propanols were obtained.