Synthesis of isosteric phosphono analogs of biologically active alkylphosphocholines

摘要

We describe a high yield reaction sequence for the conversion of long chain alcohols into 3-(trimethylammonio)propylphosphonates. The products are phospholipase D stable isosteric phosphono analogs of the respective alkylphosphocholines. The key step is the esterification of 3-chloropropylphosphonic acid with the respective long chain alcohols using DCC/DMAP. Deprotection and various acylations of 2-hydroxy and 2-amino groups following the introduction of the headgroup are described. [References: 12]