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

Citation
Z. Chen et al., NOVEL METHOD TO PREPARE DIHYDROXY PERMETHYLATED BETA-CYCLODEXTRIN ISOMERIC INTERMEDIATES FOR BIFUNCTIONAL ENZYME MIMICS, Journal of organic chemistry, 62(24), 1997, pp. 8529-8534
Citations number
30
Language
INGLESE
art.tipo
Article
ISSN journal
0022-3263
Volume
62
Issue
24
Year of publication
1997
Pages
8529 - 8534
Database
ISI
SICI code
0022-3263(1997)62:24<8529:NMTPDP>2.0.ZU;2-D
Abstract
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.