72151-03-2Relevant articles and documents
Photochemically immobilized 4-methylbenzoyl cellulose as a powerful chiral stationary phase for enantioselective chromatography
Francotte, Eric,Huynh, Dan,Zhang, Tong
, (2016/12/30)
A process to immobilize para-methylbenzoyl cellulose (PMBC) on silica gel has been developed and applied to prepare chiral stationary phases (CSPs) for enantioselective chromatography. The immobilization was achieved by simple irradiation of the polysaccharide derivative with ultraviolet light after coating on a silica gel support. The influence of parameters such as irradiation time and solvent on immobilization effectiveness were investigated. The performance of the prepared immobilized phases were evaluated by injection of a series of racemic compounds onto the packed columns and determination of their chiral recognition ability. By contrast to the classical coated phase, the immobilized CSP can be used under various chromatographic conditions without limitation of organic solvent types as the mobile phase. This extended applicability permits to improve selectivity and to resolve chiral compounds which are not or only poorly soluble in the mobile phases which are compatible with the non-immobilized PMBC stationary phase.
Synthesis and Enantioseparation Ability of Xylan Bisphenylcarbamate Derivatives as Chiral Stationary Phases in HPLC
Li, Geng,Shen, Jun,Li, Qiang,Okamoto, Yoshio
, p. 518 - 522 (2015/08/03)
Ten novel xylan bisphenylcarbamate derivatives bearing meta- and para-substituents on their phenyl groups were synthesized and their chiral recognition abilities were evaluated as the chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) after coating them on macroporous silica. The chiral recognition abilities of these CSPs depended on the nature, position, and number of the substituents on the phenyl moieties. The introduction of an electron-donating group was more attractive than an electron-withdrawing group to improve the chiral recognition ability of the xylan phenylcarbamate derivatives. Among the CSPs discussed in this study, xylan bis(3,5-dimethylphenylcarbamate)-based CSP seems to possess the highest resolving power for many racemates, and the meta-substituted CSPs showed relatively better chiral recognition than the para-substituted ones. For some racemates, the xylan bis(3,5-dimethylphenylcarbamate) derivative exhibited higher enantioselectivity than the CSP based on cellulose tris(3,5-dimethylphenylcarbamate). Chirality 27:518-522, 2015
Immobilization and chromatographic evaluation of novel regioselectively substituted amylose-based chiral packing materials for HPLC
Shen, Jun,Li, Pengfei,Liu, Shuangyan,Shen, Xiande,Okamoto, Yoshio
scheme or table, p. 878 - 886 (2012/06/30)
The regioselectively substituted amylose derivatives bearing a 4-tert-butylbenzoate or 4-chlorobenzoate group at 2-position, and 3,5-dichlorophenylcarbamate and a small amount of 3-(triethoxysilyl) propylcarbamate groups at 3- and 6-positions were synthesized by a two-step process based on the esterification of 2-position of a glucose unit. The obtained derivatives were effectively immobilized onto macroporous silica gel by intermolecular polycondensation of triethoxysilyl groups. Their chiral recognition abilities were evaluated as chiral packing materials (CPMs) for high-performance liquid chromatography. These CPMs showed high chiral recognition as well as the conventional coated-type CPM, and can be used with the eluents-containing chloroform and tetrahydrofuran. With the extended use of these eluents, improvement of chiral recognition and reversed elution orders were realized. For some racemates, the immobilized CPM exhibited ability comparable or better to the commercial immobilized amylose- or cellulose-based columns,