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Regioselective Silylations of C-2 Hydroxyl Groups of Cyclodextrins Dependent on Reaction Temperature

Katsunori Teranishi; Fumiko Ueno

Journal of Inclusion Phenomena and Macrocyclic Chemistry 44(1-4): 307-312

2002

ISSN/ISBN: 1388-3127
DOI: 10.1023/a:1023027005243
Accession: 063112088
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Silylations of the C-2 hydroxyl group of cyclodextrins were carried out using t-butyldimethylsilyl imidazole in the presence of 4A molecular sieves in N,N-dimethylformamide. A unique aspect of this silylation method is the temperature dependence of the regioselectivity; silylation at 0 °C regioselectively favored the C-6 position to afford mono-6-O-t-butyldimehylsilyl-cyclodextrins, whereas silylation at 140 °C exhibited high regioselectivity on the C-2 hydroxyl group.

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