NEW PERMETHYL-SUBSTITUTED BETA-CYCLODEXTRIN POLYSILOXANES FOR USE AS CHIRAL STATIONARY PHASES IN OPEN-TUBULAR COLUMN CHROMATOGRAPHY

takis(2,3-di-O-methyl)-6-O-tosyl-beta-cyclodextrin (2) was prepared fr om heptakis(2,3-di-O-methyl)-beta-cyclodextrin (1) in a 31 % yield. Th e tosyl group of 2 was substituted by p-(allyloxy)phenyl in a yield of 74 % to produce phenyl)heptakis(2,3-di-O-methyl)-beta-cyclodextrin (3 ). This material was derivatized at the other 6-positions to produce p ersubstituted 6A-O-(p-(allyloxy)phenyl)-beta-cyclodextrins 4, 5, and 8 . Permethylated 6-O-tosyl-beta-cyclodextrin 9, which was used for the preparation of 10-12, was obtained from 2 almost quantitatively. ilyl) -(heptakis(2,3-di-O-methyl)-beta-cyclodextrin (13) was also obtained f rom 1 in a 33% yield. Permethylated 6A-deoxy-6A-methylene-beta-cyclode xtrin (17) was prepared from 13 by a 4-step process. Seven new permeth yl-substituted beta-cyclodextrins bound to polymethylsiloxane were pre pared by a hydrosilylation reaction of the permethyl-substituted monoa lkenyl-beta-cyclodextrins with polyhydromethylsiloxane. The polymeric phases provide excellent enantiomeric separation of a variety of chira l solutes in open tubular column supercritical fluid chromatography (S FC) and gas chromatography (GC).