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Reactivity Tournament of Isothiocyanato-Functionalized Saccharides with 1,6-Diamino-3,6-oxaoctane

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Timely Research Perspectives in Carbohydrate Chemistry

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Summary

Thiourea-bridged glycoclusters and glycodendrimers are described in the literature as mimetics of (oligoantennary) oligosaccharides to serve as high-affinity lectin ligands. In extension of this concept, the assembly of different, structurally varied isothiocyanato-functionalized sugar derivatives on an oligoamine scaffold would lead to novel mixed glycoclusters. To control this approach, the relative reactivities of the isothiocyanates used in the thiourea-bridging reaction have to be known. Therefore, competition experiments with six different sugar isothiocyanates were carried out using 1,8-diamino-3,6-dioxaoctane as a symmetrical difunctionalized core molecule. Reactivities were ranked on the basis of integration ratios in the 1H NMR spectra. A first mixed thiourea-bridged glycocluster was successfully prepared.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Christiana Albertina University of Kiel, D-24098, Kiel, Germany

    Mark Walter & Thisbe K. Lindhorst

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  1. Mark Walter
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  2. Thisbe K. Lindhorst
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Editors and Affiliations

  1. Institute of Organic Chemistry, University of Vienna, Vienna, Austria

    Walther Schmid

  2. Institute of Organic Chemistry, Technical University of Graz, Graz, Austria

    Arnold E. Stütz

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© 2002 Springer-Verlag Wien

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Walter, M., Lindhorst, T.K. (2002). Reactivity Tournament of Isothiocyanato-Functionalized Saccharides with 1,6-Diamino-3,6-oxaoctane. In: Schmid, W., Stütz, A.E. (eds) Timely Research Perspectives in Carbohydrate Chemistry. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6130-2_8

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  • DOI: https://doi.org/10.1007/978-3-7091-6130-2_8

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-7289-6

  • Online ISBN: 978-3-7091-6130-2

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