POLYMERIC CHIRAL CROWN ETHERS .7. SYNTHESIS OF POLYMERS INCORPORATING METHYL GLYCOSIDES OF ALPHA-D-ALTROSE, ALPHA-D-GALACTOSE, ALPHA-D-GLUCOSE AND ALPHA-D-MANNOSE RESIDUES VIA COPOLYMERIZATION OF DIVINYL ETHERS

Polymers with chiral asymmetric crown ether units (5,6,7 and 8) were synthesized via cationic cyclopolymerization of methyl 2,3-bis{O-[2-(2-vinyloxyethoxy)ethyl]}-4,6-O-benzylidene alpha-D-altro-, alpha-D-galacto-, alpha-D-gluco- and alpha-D-mannopyranosides (1, 2, 3 and 4), respectively. The enantioselective transport of the methyl ester of phenylglycine (PhGlyOCH3) and phenylalanine (PhAlaOCH3) was examined through a bulk chloroform solution of chiral polymers from one aqueous solution to another. The transport rate of PhAlaOCH3 was larger than that of PhGlyOCH3 for every host polymer. For polymer 7, the optical purity of PhAlaOCH3 transported from one to the other phase was 12,6%, and the ratio of rate constants for the faster moving enantiomer A and the slower moving enantiomer B (k(A)*/k(B*) was 1,48. The faster moving enantiomer was the L-isomer except for the systems polymer 7 - PhAlaOCH3 and polymer 8 - PhAlaOCH3. This enantioselectivity is caused by the diastereotopic faces of the crown ether units in the host polymers.