Asymmetric Synthesis of the 3-TOSU Monomer

Abstract

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.

Meeting Name

246th National Meeting of the American-Chemical-Society (2013: Sep. 8-12, Indianapolis, IN)

Department(s)

Chemistry

International Standard Serial Number (ISSN)

0065-7727

Document Type

Article - Conference proceedings

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2013 American Chemical Society (ACS), All rights reserved.

Publication Date

12 Sep 2013

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