Substituted cyclodextrins and process for chromatographic separation of chiral organic compounds

Abstract

Substituted cyclodextrins of the general formula ##STR1## in which R.sup.2 and R.sup.6 mean straight-chain or branched alkyl or alkenyl groups with 1 to 8 carbon atoms or cycloalkyl groups with 5 to 8 carbon atoms which can be the same or different, andR.sup.3 represents a straight-chain or branched alkyl or alkenyl group, which can be the same or different to the residues R.sup.2 and R.sup.6, with 1 to 8 carbon atoms or a cycloalkyl group with 5 to 8 carbon atoms, oran acyl group with an optionally substituted, saturated or olefinically unsaturated aliphatic or cycloaliphatic or with an aromatic hydrocarbon residue with 1 to 8 carbon atoms, andn=6 or 7,a process for their production, and a process for the separation of chiral organic compounds by chromatographic separation processes in which the substituted cyclodextri are used as stationary phase.

Claims

2. A substituted cyclodextrin according to claim 1, wherein the alkyl and/or acyl groups have 3 to 6 carbon atoms.

3. A subsututed cyclodextrin according to claim 1, wherein R.sup.2, R.sup.3 and R.sup.6 are alkyl or alkenyl groups with 3 to 6 carbon atoms or R.sup.3 may be an acetyl group.

4. A substituted cyclodextrin according to claim 1, wherein R.sup.2 and R.sup.6 each is e n-pcntyl-group and R.sup.3 is an acetyl group.

5. A process for the production of a substituted cyclodextrin according to claim 1, which comprises dissolving an.alpha.- or.beta.-cyclodextrin in an anhydrous solvent, adding a pulverted alkali hydroxide, and reacting the cyclodextrin with an alkyl halide.

6. A process according to claim 5, including the further step of reacting the product with an acylating agent in an anhydrous solvent containing an amine.

7. A process according to claim 5 wherein the anhydrous solvent is aprotic.