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

Abstract

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. magnified image