Carbohydrate Modified Polydimethylsiloxanes. Part 1. Synthesis and Characterization of Carbohydrate Silane and Siloxane Building Blocks

A series of silanes containing carbohydrate residues usable as building blocks for the preparation of modified poly(dimethylsiloxane)s (PDMS) were synthesized. Allyl glycosides, allyl ethers and allyl amides of glucose, gluconic acid and glucuronic acid-γ-lactone with protected hydroxyl groups were reacted with diisopropoxymethylsilane in the presence of hydrosilylation catalysts yielding sugar substituted dialkoxysilanes. In addition, di- and trialkoxysilanes containing sugar residues were obtained by reaction of D(+)glucono-δ-lactone with 3-aminopropylsilanes. By hydrosilylation of tetramethylcyclotetrasiloxane with trimethylsilyl (TMS)-protected 3-O-allylglucose a glucose substituted cyclosiloxane was obtained and used in equilibration reactions for the synthesis of water soluble PDMS with pendant sugar moieties. However, the ring double bond of cellobial was found to be unaccessible for hydrosilylations.