Synthesis of regioselectively substituted cellulose derivatives and applications in chiral chromatography
Synthesis of regioselectively substituted cellulose derivatives and applications in chiral chromatography
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DOI：
10.1002/(sici)1520-636x(1998)10:4
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发表时间：
1998-01-01
期刊：
影响因子：
2
通讯作者：
Mak, CP
中科院分区：
文献类型：
--
作者：
Acemoglu, M;Kusters, E;Mak, CP
合成了多种纤维素-2，3-双芳基氨基甲酸酯-6-O-芳基酯和纤维素-2，3-双芳基酯-6-O-芳基氨基甲酸酯，以测试已知的三芳基氨基甲酸酯和三芳基酯类化合物可能的组合效应，并在O-C（6）处具有高区域选择性，研究了它们作为液相色谱对映体分离的CSP的应用。将用合成的CSP获得的分离与在自填充参比柱上实现的分离进行比较，所述自填充参比柱由作为CSP标准品的纤维素-三-（3，5-二甲基苯基-氨基甲酸酯）组成。在合成的区域选择性取代的纤维素衍生物中，2，3-双-O-（3，5-二甲基苯基氨基甲酸酯）-6-O-苯甲酸酯-纤维素和2，3-双-O-（苯甲酸酯）-6-O-（3，5-二氯苯基氨基甲酸酯）-纤维素给出了用于分离测试外消旋体的最佳CSP。来自区域选择性取代的纤维素衍生物的CSP对于某些类别的外消旋化合物似乎表现出比纤维素-三-（3，5-二甲基苯基氨基甲酸酯）更高的选择性。(C)1998 Wiley-Liss，Inc.
Various cellule se-2,3-bis-arylcarbamate-6-O-arylesters and cellule se-2,3-bis-arylester-6-O-arylcarbamates, designed to test the possible combined effects of the known tris-arylcarbamate and trisarylester classes, were synthesized with high regioselectivity at O-C(6), and their use as CSPs in liquid chromatography for enantiomeric separations was investigated. The separations obtained with the synthesized CSPs were compared to the separations achieved on a self-packed reference column, consisting of cellulose-tris-(3,5-dimethylphenyl-carbamate) as CSP standard. Among the synthesized, regioselectively substituted cellulose derivatives, 2,3-bis-O-(3,5-dimethylphenylcarbamate)-6-O-benzoate-cellulose and 2,3-bis-O-(benzoate)-6-O-(3,5-dichlorophenyl-carbamate)-cellulose gave the best CSPs for the separation of the test racemates. CSPs from regioselectively substituted cellulose derivatives seem to exhibit higher selectivities than cellulose-tris-(3,5-dimethylphenylcarbamate) for certain classes of racemic compounds. (C) 1998 Wiley-Liss, Inc.