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Syntheses of Well-Defined Glyco-Polyorganosiloxanes by “Click” Chemistry and their Surfactant Properties

✍ Scribed by Sami Halila; Maggy Manguian; Sébastien Fort; Sylvain Cottaz; Thierry Hamaide; Etienne Fleury; Hugues Driguez

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
284 KB
Volume
209
Category
Article
ISSN
1022-1352

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✦ Synopsis

Abstract

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.

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