Silicon-Modified Carbohydrate Surfactants I: Synthesis of Siloxanyl Moieties Containing Straight-chained Glycosides and Amides

New siloxanyl-modified carbohydrate surfactants of the amide and glycoside type have been synthesized by coupling between defined as well as higher-molecular-weight siloxanes and carbohydrate structures via spacers of different lengths and hydrophilic power. Linear and branched monohydrogen di-, tri-, tetra- and penta-siloxanes and polyhydrogen siloxanes as well as mono- and di-saccharide lactone structures have been found to be good starting materials for the synthesis of amides, often in quantitative yield, whereas glycosides had to be prepared in low-yield multistep sequences including protection/deprotection steps. Selected strategies were applied to polysiloxanes yielding quantitatively a broad variety of carbohydrate-modified comb-like structures. The new substances were characterized by means of ¹³C NMR spectroscopy, GC, capillary GC, GC–MS coupling and elemental analysis.