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Issue 14, 2005
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A new approach to A,B-difunctionalisation of cyclodextrins using bulky 1,3-bis[bis(aryl)chloromethyl]benzenes as capping reagents

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Abstract

1,3-Bis[bis(4-tert-butylphenyl)chloromethyl]benzene and 1,3-bis[bis(4-anisyl)chloromethyl]benzene were employed as regioselective capping reagents for the preparation of C-6A,C-6B-bridged, permethylated α- and β-CD derivatives; isolated yields up to 55% of proximally capped, methylated CDs were obtained, thus opening the way to the straightforward preparation of a wide range of A,B-functionalised CDs. As revealed by a single crystal X-ray diffraction study, the benzene-1,3-bis[bis(4-tert-butylphenyl)methyl] spacer is perfectly suited for A,B-capping of β-cyclodextrin.

Graphical abstract: A new approach to A,B-difunctionalisation of cyclodextrins using bulky 1,3-bis[bis(aryl)chloromethyl]benzenes as capping reagents

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Publication details

The article was received on 21 Mar 2005, accepted on 23 May 2005 and first published on 10 Jun 2005


Article type: Paper
DOI: 10.1039/B504012D
Citation: Org. Biomol. Chem., 2005,3, 2588-2592
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    A new approach to A,B-difunctionalisation of cyclodextrins using bulky 1,3-bis[bis(aryl)chloromethyl]benzenes as capping reagents

    D. Armspach, L. Poorters, D. Matt, B. Benmerad, F. Balegroune and L. Toupet, Org. Biomol. Chem., 2005, 3, 2588
    DOI: 10.1039/B504012D

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