Hydrolytically stable linkers for silicone carbohydrates derived from hydrodiisopropylsilanes |
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Authors: | David B Thompson Ferdinand Gonzaga Amanda S Fawcett Michael A Brook |
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Institution: | (1) Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, L8S 4M1, Canada |
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Abstract: | 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. |
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Keywords: | Silane linker Silicone-carbohydrate Hydrolytic stability Difunctional silane Hydrosilylation |
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