Study on Synthesis and NMR Characterization of 2,3-O-Hydroxyethyl Cellulose Depending on Synthesis Conditions

Authors

  • Katrin Petzold-Welcke,

    1. Friedrich Schiller University of Jena, Institute for Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstrasse 10, D-07743 Jena, Germany
    Search for more papers by this author
  • Manuela Kötteritzsch,

    1. Friedrich Schiller University of Jena, Institute for Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstrasse 10, D-07743 Jena, Germany
    Search for more papers by this author
  • Dominik Fenn,

    1. present address: Almenweg 18, D-67657 Kaiserslautern, Germany
    Search for more papers by this author
  • Andreas Koschella,

    1. Friedrich Schiller University of Jena, Institute for Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstrasse 10, D-07743 Jena, Germany
    Search for more papers by this author
  • Thomas Heinze

    Corresponding author
    1. Friedrich Schiller University of Jena, Institute for Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstrasse 10, D-07743 Jena, Germany
    • Friedrich Schiller University of Jena, Institute for Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstrasse 10, D-07743 Jena, Germany, Fax +49 3641 948 272.
    Search for more papers by this author
    • Member of the European Polysaccharide Network of Excellence (EPNOE), www.epnoe.eu


Abstract

The synthesis of hydroxyethyl celluloses with regioselective functionalization in position 2 and 3 starting from triphenylmethyl (trityl) cellulose is described. The effects of reaction conditions upon both the degree of substitution and the distribution of the hydroxyethyl moieties were investigated in detail. The interest was not only focused on regioselective functionalization within the anhydroglucose unit but also on the formation of oxyethylene side chains. To avoid the formation of oxyethylene side chains, 2-(2-bromoethoxy)tetrahydropyran was used as etherifying agent in comparison with 2-bromoethanol. By acidic hydrolysis, both protecting groups – trityl at 6 position and tetrahydropyran at the hydroxyethyl substituent – can be simultaneously cleaved off. The hydroxyethyl celluloses were characterized by one- and two-dimensional NMR spectroscopy in order to determine the substitution pattern.

Ancillary