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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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Article information


Submitted
21 Mar 2005
Accepted
23 May 2005
First published
10 Jun 2005

Org. Biomol. Chem., 2005,3, 2588-2592
Article type
Paper

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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