
TY  - JOUR
A1  - Bansal, Paramjit S. 
A1  - Francis, Craig L. 
A1  - Hart, Noel K. 
A1  - Henderson, Scott A. 
A1  - Oakenfull, David 
A1  - Robertson, Alan D. 
A1  - Simpson, Gregory W. 
T1  - Regioselective Alkylation of &#946;-Cyclodextrin
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1998
VL  - 51
IS  - 10
SP  - 915
EP  - 924
KW  - 
UR  - https://doi.org/10.1071/C98064 
N2  - 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. 
ER  -

