N-Methoxycarbonyl chitosan was prepared by selectively modifying the amino group at the 2-position of chitosan with methyl chloroformate, which was further functionalized with p-methylbenzylamine to produce chitosan (p-methylbenzylurea). Then, the hydroxyl groups at the 3- and 6-positions of the glucose skeleton were modified with various phenyl isocyanates, affording a series of chitosan 3,6-bis(arylcarbamate)-2-(p-methylbenzylurea)s, which were characterized and proposed as chiral selectors for enantiomer separation. Nineteen racemates, most of which are drugs or intermediates for drugs, were selected as the model analytes to evaluate the enantioseparation performance. The structure-performance relationship of the chiral selectors was investigated in detail. It was found that the methyl-substituted chiral selectors possessed more preferable enantioseparation performance compared with the chloro-substituted ones, and the chiral selectors containing a methyl substituent at the 4-position of the benzene ring showed the best chiral recognition and separation ability with 17 racemates being recognized and 13 racemates being baseline separated. The prepared chiral separation materials derived from these chiral selectors exhibited favorable solvent tolerance towards ethyl acetate, acetone, chloroform and a low proportion of tetrahydrofuran in normal phase. To sum up, this work provided a useful reference for the design and preparation of high-performance chiral separation materials for efficient enantiomer separation.

N-甲氧羰基壳聚糖是通过用氯甲酸甲酯选择性修饰壳聚糖2位上的氨基来制备的，再用对甲基苄胺将其官能化以生产壳聚糖（对甲基苄基脲）。然后，用各种异氰酸苯酯修饰葡萄糖骨架3位和6位的羟基，得到一系列壳聚糖3,6-双（芳基氨基甲酸酯）-2-（p-甲基苄基脲，已被表征并建议用作对映异构体分离的手性选择剂。选择19个外消旋体（其中大多数是药物或药物中间体）作为模型分析物，以评估对映体分离性能。详细研究了手性选择剂的结构-性能关系。发现与氯取代的手性选择剂相比，甲基取代的手性选择剂具有更优选的对映体分离性能，并且在苯环的4位上含有甲基取代基的手性选择剂表现出最佳的手性识别和分离能力，为17识别出消旋体，基线分离出13个消旋体。衍生自这些手性选择剂的制备的手性分离材料在正相中对乙酸乙酯，丙酮，氯仿和低比例的四氢呋喃表现出有利的溶剂耐受性。综上所述，这项工作为设计和制备用于高效对映异构体分离的高性能手性分离材料提供了有用的参考。