
%0 Journal Article
%A Bansal, Paramjit S. 
%A Francis, Craig L. 
%A Hart, Noel K. 
%A Henderson, Scott A. 
%A Oakenfull, David 
%A Robertson, Alan D. 
%A Simpson, Gregory W. 
%T Regioselective Alkylation of &#946;-Cyclodextrin
%J Australian Journal of Chemistry
%D 1998/10/07
%V 51
%N 10
%P 915-924
%K 
%R https://doi.org/10.1071/C98064
%U https://www.publish.csiro.au/paper/C98064 
%X Methodology for preparation of heptakis(2,6-di-O-alkyl)-&#946;-cyclodextrins, heptakis(2-O-alkyl)-&#946;- cyclodextrins, and heptakis(6-O-alkyl)-&#946;-cyclodextrins in substantially purified form has been developed. Treatment of &#946;-cyclodextrin (1) with sodium or barium hydroxide and various alkyl halides in dimethyl sulfoxide or a mixture of dimethyl sulfoxide and N,N-dimethylformamide provided the corresponding heptakis(2,6-di-O-alkyl)-&#946;-cyclodextrins. Treatment of heptakis(6-O-t-butyldimethylsilyl)-&#946;-cyclodextrin (5) with sodium hydroxide and several haloalkanes in dimethyl sulfoxide followed by desilylation provided heptakis(2-O-alkyl)-&#946;-cyclodextrins. Protection of the secondary hydroxy groups of the t-butyldimethylsilyl-&#946;-cyclodextrin (5) as benzyl ethers, followed by desilylation, alkylation, and debenzylation afforded several heptakis(6-O-alkyl)-&#946;-cyclodextrins. Analytical methodology has been developed to characterize all of these compounds, with the homogeneity of the pattern of substitution verified by h.p.l.c. analysis, f.a.b.&#8211;mass spectrometry and n.m.r. spectroscopy. 
