A new mixed acetal-type substitution pattern for alpha-cyclodextrin. Preparation of hexakis (3-O-benzyl)- alpha-cyclodextrin |
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| Authors: | Lipták A Jánossy L Batta G Borbás A Szejtli J |
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| Institution: | Research Group for Carbohydrates of the Hungarian Academy of Sciences, Institute of Biochemistry, L. Kossuth University, Debrecen. liptaka@tigris.klte.hu |
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| Abstract: | alpha-CD was converted into hexakis2,6-di-O-(methoxydimethyl)methyl]-alpha-CD by a proton-catalyzed reaction with 2-methoxypropene. Subsequent benzylation under Brimacombe conditions resulted in the fully protected compound, from which the acid-sensitive acetal groups were removed to obtain hexakis(3-O-benzyl)-alpha-cyclodextrin. The structure of all of the compounds synthesized was confirmed by 13C J-ECHO, COSY, HETCOR and HMBC NMR measurements. |
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