Syntheses of well-defined glyco-polyorganosiloxanes by click chemistry and their surfactant properties

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 xyloglucooligosaccharide 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 NaN3 to afford the monoazido 6 and di-azido 8 derivatives, respectively. The coupling reaction took place in a hydro-alcoholic medium in the presence Of CuSO4/Sodium ascorbate as catalyst. Only one compound, MD'M-click-XGO 12 showed good solubility in water with interesting surfactant properties.