Water-soluble 3-O-(2-methoxyethyl)cellulose: synthesis and characterization

Carbohydr Res. 2008 Mar 17;343(4):668-73. doi: 10.1016/j.carres.2008.01.018. Epub 2008 Jan 26.

Abstract

The synthesis of novel 3-O-(2-methoxyethyl)cellulose via 2,6-di-O-thexyldimethylsilyl ethers was successfully carried out. Treatments of 3-O-(2-methoxyethyl)-2,6-di-O-thexyldimethylsilylcellulose with tetrabutylammonium fluoride trihydrate led to a complete removal of the protecting groups. Structure characterization carried out by means of 1D and 2D NMR spectroscopy proves a high regioselectivity. The novel cellulose ether is soluble in dimethyl sulfoxide, N,N-dimethylacetamide, N-methylpyrrolidone, and water. Size-exclusion chromatography revealed a distinct aggregation behavior in water.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cellulose / analogs & derivatives
  • Cellulose / chemical synthesis*
  • Cellulose / chemistry
  • Chromatography, Gel
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Solubility
  • Water / chemistry*

Substances

  • 3-O-(2-methoxyethyl)cellulose
  • Water
  • Cellulose