NOVEL METHOD TO PREPARE DIHYDROXY PERMETHYLATED BETA-CYCLODEXTRIN ISOMERIC INTERMEDIATES FOR BIFUNCTIONAL ENZYME MIMICS

Natural beta-cyclodextrin was treated with 3.5 equiv of tert-butyldime thylsilyl chloride and then with NaH and MeI in the same reaction vess el to give a mixture of oligosilyl-substituted permethylated beta-cycl odextrins. The mixture was treated with NH4F and the resulting 6(A),6( D)-(1), 6(A),6(C)-(2), and 6(A),6(B)-(3) dihydroxy permethylated beta- cyclodextrins were isolated in 7.6-8.9% yields by two silica gel chrom atographic separations. The structures of 1-3 were verified by compari son of spectral properties with a known diol (2) or preparing known de rivatives (1 and 3). This is a superior way to prepare and isolate dih ydroxy permethylated beta-cyclodextrin intermediates for bifunctional enzyme mimics.