Synthesis of enantiomerically pure lysophosphatidylinositols and alkylphosphoinositols

A convenient synthesis for enantiomeric pure

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,

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(or and (or has been described. Starting from myo-inositol, penta-O-acetyl-myo-inositol was made in five steps. Then enantiomeric purification was done by a diastereomeric salts separation method, and the purity of each enantiomer was spectroscopically measured (¹⁹F-NMR). The phosphodiester was made via phosphoramidites. The enantiomeric products (>99% optical purity) of all compounds were easily obtained in large quantities (5–10 g). Synthetic phosphatidylinositol analogues of precisely defined structure and configuration are interesting tools for studying signal transduction mechanism and cell activity modulation.