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Syntheses of Well‐Defined Glyco‐Polyorganosiloxanes by “Click” Chemistry and their Surfactant Properties
Author(s) -
Halila Sami,
Manguian Maggy,
Fort Sébastien,
Cottaz Sylvain,
Hamaide Thierry,
Fleury Etienne,
Driguez Hugues
Publication year - 2008
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200700629
Subject(s) - click chemistry , cycloaddition , chemistry , pulmonary surfactant , polymer chemistry , solubility , azide , sodium azide , 1,3 dipolar cycloaddition , organic chemistry , catalysis , biochemistry
Well‐defined glyco‐polyorganosiloxanes were synthesized by the Cu( I )‐catalyzed Huisgen 1,3‐dipolar cycloaddition reaction (often simply referred to as “click” chemistry). N ‐propargylglycosylamines 2 and 4 were first synthesized from cellobiose ( 1 ) and xylogluco‐oligosaccharide XGOs 3 without protecting groups. The azide function was introduced into polydimethylsiloxanes [PDMS: 5 (MD′M) and 7 (M′DM′)] by azidolysis of the counterpart epoxy silicon with NaN 3 to afford the mono‐azido 6 and di‐azido 8 derivatives, respectively. The coupling reaction took place in a hydro‐alcoholic medium in the presence of CuSO 4 /sodium ascorbate as catalyst. Only one compound, MD′M‐“click”‐XGO 12 showed good solubility in water with interesting surfactant properties.