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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective double capping of cyclodextrin scaffolds.

Rafael Gramage-Doria1, David Rodriguez-Lucena, Dominique Armspach

  • 1Laboratoire de Chimie Inorganique et Catalyse, Institut de Chimie UMR 7177 CNRS, Université de Strasbourg, Strasbourg, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 3, 2011
PubMed
Summary

Researchers developed four regioselective double capping reactions for cyclodextrins (CDs). These methods efficiently synthesized novel tetrafunctionalized β-CDs, C(1)-symmetrical β-CDs, and α-/β-CDs with sulfate handles, favoring proximal capping.

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Area of Science:

  • Carbohydrate Chemistry
  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Cyclodextrins (CDs) are versatile cyclic oligosaccharides with unique host-guest properties.
  • Regioselective functionalization of CDs is crucial for developing advanced materials and applications.
  • Developing efficient methods for double capping of CDs remains a synthetic challenge.

Purpose of the Study:

  • To explore novel regioselective double capping reactions for α- and β-cyclodextrins.
  • To synthesize unprecedented functionalized cyclodextrin derivatives.
  • To investigate the regioselectivity and efficiency of different capping reagents.

Main Methods:

  • Application of four distinct regioselective double capping reactions.
  • Utilized rigid, bulky dialkylating reagents, PhP(2-), and S(2-) dianions.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy and single-crystal X-ray diffraction.

Main Results:

  • Successful synthesis of an A,B,D,E-tetrafunctionalised β-CD regioisomer on a large scale.
  • Preparation of new C(1)-symmetrical β-CDs linked by short spacers.
  • High-yield synthesis of α- and β-CDs featuring two sulfate handles.
  • Demonstrated a preference for proximal capping with the employed difunctional reagents.

Conclusions:

  • Developed versatile synthetic routes for regioselectively double-capped cyclodextrins.
  • The new derivatives offer potential for novel supramolecular assemblies and applications.
  • Thorough structural elucidation confirmed the successful synthesis and regiochemistry.