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Lepage ML, Schneider JP, Bodlenner A, et al. Toward a Molecular Lego Approach for the Diversity-Oriented Synthesis of Cyclodextrin Analogues Designed as Scaffolds for Multivalent Systems. J Org Chem. 2015;80(21):10719-33doi: 10.1021/acs.joc.5b01938.
Lepage, M. L., Schneider, J. P., Bodlenner, A., & Compain, P. (2015). Toward a Molecular Lego Approach for the Diversity-Oriented Synthesis of Cyclodextrin Analogues Designed as Scaffolds for Multivalent Systems. The Journal of organic chemistry, 80(21), 10719-33. https://doi.org/10.1021/acs.joc.5b01938
Lepage, Mathieu L, et al. "Toward a Molecular Lego Approach for the Diversity-Oriented Synthesis of Cyclodextrin Analogues Designed as Scaffolds for Multivalent Systems." The Journal of organic chemistry vol. 80,21 (2015): 10719-33. doi: https://doi.org/10.1021/acs.joc.5b01938
Lepage ML, Schneider JP, Bodlenner A, Compain P. Toward a Molecular Lego Approach for the Diversity-Oriented Synthesis of Cyclodextrin Analogues Designed as Scaffolds for Multivalent Systems. J Org Chem. 2015 Nov 06;80(21):10719-33. doi: 10.1021/acs.joc.5b01938. Epub 2015 Oct 26. PMID: 26439895.
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J Org Chem. 2015 Nov 06;80(21):10719-33. doi: 10.1021/acs.joc.5b01938. Epub 2015 Oct 26.

Toward a Molecular Lego Approach for the Diversity-Oriented Synthesis of Cyclodextrin Analogues Designed as Scaffolds for Multivalent Systems.

The Journal of organic chemistry

Mathieu L Lepage, Jérémy P Schneider, Anne Bodlenner, Philippe Compain

Affiliations

  1. Laboratoire de Synthèse Organique et Molécules Bioactives, Université de Strasbourg/CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux , 25 rue Becquerel, 67087 Strasbourg, France.
  2. Institut Universitaire de France , 103 Bd Saint-Michel, 75005 Paris, France.

PMID: 26439895 DOI: 10.1021/acs.joc.5b01938

Abstract

A modular strategy has been developed to access a diversity of cyclic and acyclic oligosaccharide analogues designed as prefunctionalized scaffolds for the synthesis of multivalent ligands. This convergent approach is based on bifunctional sugar building blocks with two temporarily masked functionalities that can be orthogonally activated to perform Cu(I)-catalyzed azide-alkyne cycloaddition reactions (CuAAC). The reducing end is activated as a glycosyl azide and masked as a 1,6-anhydro sugar, while the nonreducing end is activated as a free alkyne and masked as a triethylsilyl-alkyne. Following a cyclooligomerization approach, the first examples of close analogues of cyclodextrins composed of d-glucose residues and triazole units bound together through α-(1,4) linkages were obtained. The cycloglucopyranoside analogue containing four sugar units was used as a template to prepare multivalent systems displaying a protected d-mannose derivative or an iminosugar by way of CuAAC. On the other hand, the modular approach led to acyclic alkyne-functionalized scaffolds of a controlled size that were used to synthesize multivalent iminosugars.

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