Novel 3-mono-O-hydroxyethyl cellulose: synthesis and structure characterization

The synthesis of 3-mono-O-hydroxyethyl cellulose using orthogonal protecting groups was realized. The reaction of 2,6-di-O-thexyldimethylsilyl cellulose with 2-(2-bromoethoxy)tetrahydropyran leads to a completely functionalized cellulose derivative. The complete removal of the protecting groups was...

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Bibliographic Details
Published in:Cellulose (London) 2009-10, Vol.16 (5), p.853-861
Main Authors: Fenn, Dominik, Heinze, Thomas
Format: Article
Language:English
Subjects:
Bioorganic Chemistry
Cellulose
Ceramics
Chemistry
Chemistry and Materials Science
Composites
Gelation
Glass
Hydrochloric acid
Hydroxyethyl celluloses
Natural Materials
NMR spectroscopy
Organic Chemistry
Physical Chemistry
Polymer Sciences
Structural analysis
Sustainable Development
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Summary:The synthesis of 3-mono-O-hydroxyethyl cellulose using orthogonal protecting groups was realized. The reaction of 2,6-di-O-thexyldimethylsilyl cellulose with 2-(2-bromoethoxy)tetrahydropyran leads to a completely functionalized cellulose derivative. The complete removal of the protecting groups was possible by split off of the TDMS functions with tetrabutylammonium fluoride trihydrate and subsequently the tetrahydropyran moieties with hydrochloric acid. The structure of 3-mono-O-hydroxyethyl cellulose was confirmed by applying one and two-dimensional NMR spectroscopy. The novel polymer is soluble in water and does not show thermoreversible gelation.
ISSN:0969-0239
1572-882X
DOI:10.1007/s10570-009-9297-x