One-pot regioselective synthesis of 2I,3I-O-(o-xylylene)-capped cyclomaltooligosaccharides: tailoring the topology and supramolecular properties of cyclodextrins

Patricia Balbuena; David Lesur; M. José González Álvarez; Francisco Mendicuti; Carmen Ortiz Mellet; José M. García Fernández

doi:10.1039/B705644C

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One-pot regioselective synthesis of 2^I,3^I-O-(o-xylylene)-capped cyclomaltooligosaccharides: tailoring the topology and supramolecular properties of cyclodextrins†

Patricia Balbuena,^a David Lesur,^b M. José González Álvarez,^c Francisco Mendicuti,^c Carmen Ortiz Mellet*^a and José M. García Fernández*^d

Author affiliations

* Corresponding authors

^a Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, Sevilla, Spain
E-mail: mellet@us.es
Fax: +34 954624960
Tel: +34 954551519

^b Laboratoire des Glucides UMR6219, Université Picardie Jules Verne, 33 rue St. Leu, Amiens, France

^c Departamento de Química Física, Universidad de Alcalá, Alcalá de Henares, Spain

^d Instituto de Investigaciones Químicas, CSIC, Américo Vespucio 49, Isla de la Cartuja, Sevilla, Spain
E-mail: jogarcia@iiq.csic.es
Fax: +34-954460565
Tel: +34-954489559

Abstract

The α,α′-dibromo-o-xylylene cap has been installed at the secondary hydroxyls of a single glucopyranosyl residue in cyclodextrins in one pot and with total regioselectivity; the resulting cyclic ether acts as a removable hinge, allowing selective elaboration of the secondary face and modulating both the self-association and the inclusion capabilities of the hosts.

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Supplementary files

Experimental details, copies of the NMR spectra and procedures for evaluation of aggregation and complexing properties PDF (2127K)

Article information

DOI: https://doi.org/10.1039/B705644C
Article type: Communication
Submitted: 16 Apr 2007
Accepted: 15 May 2007
First published: 08 Jun 2007

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Chem. Commun., 2007, 3270-3272

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One-pot regioselective synthesis of 2^I,3^I-O-(o-xylylene)-capped cyclomaltooligosaccharides: tailoring the topology and supramolecular properties of cyclodextrins

P. Balbuena, D. Lesur, M. J. G. Álvarez, F. Mendicuti, C. O. Mellet and J. M. G. Fernández, Chem. Commun., 2007, 3270 DOI: 10.1039/B705644C

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