| 摘要 |
PURPOSE: Chiral crown ether-based LC chiral stationary phases and chiral columns thereof, and a method for producing the same are provided, thereby effectively carrying out optical resolution of optical isomers in bio-stimulating racemic compounds with the first amino group. CONSTITUTION: The chiral crown ether compound is represented by the formula(1), wherein R is H, alkyl or aryl; and its absolute arrangement is (R,R,R), (S,S,S), (R,S,S) or (S,R,R). The chiral crown ether-based LC chiral stationary phases are represented by the formula(2), wherein R and R' are H, alkyl or aryl; n is an integer from 1 to 16; and the absolute arrangement is (R,R,R), (S,S,S), (R,S,S) or (S,R,R). The method for producing the chiral crown ether compound of the formula(1) comprises the steps of: reacting N,N'-tetramethyltartaramide with 1-£2-(2-phenylsulfonyloxyethoxy) ethoxymethyl| benzene to prepare a compound of the formula(3); treating the compound of the formula(3) with hydrogen gas in the presence of catalyst to prepare a compound of the formula(4); reacting the compound of the formula(4) with tosyl chloride to prepare a compound of the formula(5); reacting 2,2'-disubstituted-1,1'-bi-naphtol with the compound of the formula(5) to prepare a compound of the formula(6); and hydrolyzing the compound of the formula(6). The method for producing the chiral crown ether-based LC chiral stationary phases of the formula(2) comprises the steps of: reacting the chiral crown ether compound of the formula(1) with acetyl chloride to prepare acid anhydrous compound; and reacting the acid anhydrous compound with silica gel selected from aminoalkyl silica gel, N-alkylaminoalkyl silica gel and N-arylaminoalkyl silica gel. |
