Synthesis and hplc chiral recognition of regioselectively carbamoylated cellulose derivatives

作者: Shouwan Tang , Xiaofang Li , Fang Wang , Guihua Liu , Yonglong Li

DOI: 10.1002/CHIR.21978

关键词:

摘要: Four regioselective-carbamoylated cellulose derivatives having two different substituents at 2-, 3-, and 6-position were prepared evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography. Investigations showed that the nature andarrangement of significantly influenced recognition abilities heterosubstituted each derivative exhibited characteristic enantioseparation. Some racemates better resolved on these than corresponding homogeneously substituted including a commercial CSP, Chiralcel OD. Racemic compounds shown in this study most effectively discriminated cellulose2,3-(3-chloro-4-methylphenylcarbamate)-6-(3,5-dimethylphenylcarbamate) 2,3-(3,5-dimethylphenylcarbamate)-6-(3-chloro-4-methylphenylcarbamate). Chirality, 2012. © 2011 Wiley Periodicals, Inc.

参考文章(18)
Yoshio Okamoto, Mitsunobu Kawashima, Koichi Hatada, Chromatographic resolution : XI. Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel Journal of Chromatography A. ,vol. 363, pp. 173- 186 ,(1986) , 10.1016/S0021-9673(01)83736-5
Helmut Koller, Karl-Heinz Rimböck, Albrecht Mannschreck, High-pressure liquid chromatography on triacetylcellulose Journal of Chromatography A. ,vol. 282, pp. 89- 94 ,(1983) , 10.1016/S0021-9673(00)91594-2
C. Chassaing, A. Thienpont, M.-H. Soulard, G. Felix, Regioselectivity carbamoylated polysaccharides for the separation of enantiomers in high-performance liquid chromatography Journal of Chromatography A. ,vol. 786, pp. 13- 21 ,(1997) , 10.1016/S0021-9673(97)00553-0
Kozo Tachibana, Atsushi Ohnishi, Reversed-phase liquid chromatographic separation of enantiomers on polysaccharide type chiral stationary phases. Journal of Chromatography A. ,vol. 906, pp. 127- 154 ,(2001) , 10.1016/S0021-9673(00)00955-9
Bezhan Chankvetadze, Eiji Yashima, Yoshio Okamoto, Tris(chloro- and methyl-disubstituted phenylcarbamate)s of Cellulose as Chiral Stationary Phases for Chromatographic Enantioseparation Chemistry Letters. ,vol. 1993, pp. 617- 620 ,(1993) , 10.1246/CL.1993.617
Chiyo Yamamoto, Yoshio Okamoto, Optically Active Polymers for Chiral Separation Bulletin of the Chemical Society of Japan. ,vol. 77, pp. 227- 257 ,(2004) , 10.1246/BCSJ.77.227
Jun Shen, Tomoyuki Ikai, Yoshio Okamoto, None, Synthesis and chiral recognition of novel amylose derivatives containing regioselectively benzoate and phenylcarbamate groups Journal of Chromatography A. ,vol. 1217, pp. 1041- 1047 ,(2010) , 10.1016/J.CHROMA.2009.07.027
Yuriko Kaida, Yoshio Okamoto, Optical Resolution on Regioselectively Carbamoylated Cellulose and Amylose with 3,5-Dimethylphenyl and 3,5-Dichlorophenyl Isocyanates Bulletin of the Chemical Society of Japan. ,vol. 66, pp. 2225- 2232 ,(1993) , 10.1246/BCSJ.66.2225
Shunsuke Kondo, Chiyo Yamamoto, Masami Kamigaito, Yoshio Okamoto, Synthesis and Chiral Recognition of Novel Regioselectively Substituted Amylose Derivatives Chemistry Letters. ,vol. 37, pp. 558- 559 ,(2008) , 10.1246/CL.2008.558