Analytical and semi-preparative enantioseparation of organic phosphonates on a new immobilized amylose based chiral stationary phase.
Two chiral stationary phases derived from derivatized amylose (Chiralpak AD-H and Chiralpak IA) have been used to separate the enantiomers of new diethyl benzamidoarylmethylphosphonates. The data obtained indicate that all the studied compounds could be easily baseline resolved on both columns. Owing to the different techniques involved in their preparation, the two stationary phases differ in their abilities to effect enantiomeric separation. The semi-preparative separation of all compounds was executed successfully in n-hexane/EtOH on the new immobilized Chiralpak IA column. The analytical assessment of the enantiomeric excess values of all collected fractions was higher than 97%. The stereochemical configuration for the F1 fraction of a diethyl benzamidoarylmethylphosphonate was determined by X-ray diffraction structure analysis.
Zhang
Yuping
Y
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Guiyang, China. Fax: +86-851-362-2211.
Song
Baoan
B
Bhadury
Pinaki S
PS
Hu
Deyu
D
Yang
Song
S
Shi
Xia
X
Liu
Dongmei
D
Jin
Linhong
L
D000688:Amylose / Q000737:chemistry*; D001549:Benzamides / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D063065:Organophosphonates / Q000032:analysis*; D012995:Solubility; D013237:Stereoisomerism; D013696:Temperature; D013997:Time Factors
D001549:Benzamides; D063065:Organophosphonates; D000688:Amylose