Hydrolytically stable linkers for silicone carbohydrates derived from hydrodiisopropylsilanes

Two strategies were developed for the attachment of sugars to siloxanes using bifunctional silicon linkers: the substrate could be functionalized with a silyl hydride before coupling to a vinyl-terminated siloxane through platinum catalyzed hydrosilylation; alternatively, unprotected glucose could be directly silylated by a silicone terminated with a chlorosilyl group. Optimal steric bulk was found with difunctional diisopropylsilanes, which exhibit excellent reactivity for preparation of sugarsilane derivatives, and also permit efficient grafting to silicones via hydrosilylation. The resulting product alkoxysilane-silicone exhibits greater stability to hydrolysis than the silicone itself.