A CONVENIENT SYNTHESIS OF A PERMETHYL-SUBSTITUTED BETA-CYCLODEXTRIN-CONTAINING POLYSILOXANE STATIONARY-PHASE USING AN AMIDE LINKING GROUP

A novel amide-linked permethyl-substituted beta-cyclodextrin-bound pol ysiloxane stationary phase was prepared in only four steps. First, mon o(6-O-toluenesulfonyl)-beta-cyclodextrin was treated with sodium azide . Second, the resulting azide derivative was treated with methyl iodid e and base followed by reduction with hydrogen to give amine-substitut ed permethylcyclodextrin 3. Third, cyclodextrin 3 was treated with p-( allyloxy)benzoyl chloride to form 6(A)-(p-allyloxybenzamido)-substitut ed permethyl-beta-cyclodextrin 4. Lastly, beta-cyclodextrin 4 was hydr osilylated onto a polysiloxane backbone containing hydrogen, methyl, a nd p-tolyl substituents. This new phase separated the enantiomers of c ertain chiral lactones and alcohols in capillary supercritical fluid c hromatography.