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Regioselective Double Capping of Cyclodextrin Scaffolds

Authors

  • Rafael Gramage-Doria,

    1. Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, 67008 Strasbourg cedex (France), Fax: (+33) 3-68-851-637
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  • Dr. David Rodriguez-Lucena,

    1. Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, 67008 Strasbourg cedex (France), Fax: (+33) 3-68-851-637
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  • Prof. Dominique Armspach,

    Corresponding author
    1. Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, 67008 Strasbourg cedex (France), Fax: (+33) 3-68-851-637
    • Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, 67008 Strasbourg cedex (France), Fax: (+33) 3-68-851-637
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  • Coraline Egloff,

    1. Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, 67008 Strasbourg cedex (France), Fax: (+33) 3-68-851-637
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  • Matthieu Jouffroy,

    1. Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, 67008 Strasbourg cedex (France), Fax: (+33) 3-68-851-637
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  • Dr. Dominique Matt,

    Corresponding author
    1. Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, 67008 Strasbourg cedex (France), Fax: (+33) 3-68-851-637
    • Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, 67008 Strasbourg cedex (France), Fax: (+33) 3-68-851-637
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  • Loïc Toupet

    1. Institut de Physique de Rennes UMR 6251 CNRS, Université de Rennes1, Campus de Beaulieu - Bâtiment 11 A, 35042 Rennes cedex (France)
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Abstract

Four different regioselective double capping reactions were applied either to α- or β-cyclodextrin (CD) scaffolds. The first, which relied on the use of a rigid, bulky dialkylating reagent containing two trityl-like subunits, gave access to an A,B,D,E-tetrafunctionalised β-CD regioisomer in large scale reactions. Two further capping reactions, involving the dianions PhP2− and S2−, led to the synthesis of new C1-symmetrical β-cyclodextrins in which pairs of neighbouring glucose units are linked by very short spacers. The last double capping reaction described allowed the high-yield preparation of unprecedented α- and β-cyclodextrins containing two sulfate handles. Proximal capping turned out to be favoured for each of the above difunctional reagents. The structural characterisation of the capped species was achieved by thorough NMR investigations as well as by single-crystal X-ray diffraction studies.

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