A surface reactive, organic spiroorthoester monomer ligand, [3-(9,9-diethyl-1,5,7,11-tetraoxa-spiro[5,5]undec-3-yl)-propyl]-trimethoxysilane (3-TOSU), was synthesized at a 0.1 mole scale and, with the reaction intermediates, characterized using infrared and 1H and 13C NMR spectroscopies, and mass spectrometry (GC-MS). An improved procedure for the synthesis of 3-TOSU via the corresponding thiocarbonate is described. The 3-TOSU monomer can be used to functionalize nanoparticles, whose incorporation and cure into a resulting solid 0-3 composite can produce materials of reduced polymerization stress/volume shrinkage, and bone cements of low cell toxicity and higher strength. The objective was to develop a well-characterized synthetic route to a high quality product of the 3-TOSU chemical structure.

Asymmetric synthesis of the 3-TOSU monomer

246th National Meeting (2013)

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