Phosphonolipids. XXV. Synthesis of α-Octadecyl-β-hexadecanoyl-L-α-glyceryl- (2-aminoethyl)phosphonate, a Homologue of an α-Monoether- phosphonocephalin Occurring in Tetrahymena pyriformis

Abstract

The α-monoether-phosphonocephalin isolated by Thompson and Woo from Tetrahymena pyriformis was shown to possess the L-configuration. A homologue of the natural compound, vis. α-octadecyl-β-hexadecanoyl-L-α-glyceryl-(2-aminoethyl)phosphonate, has been synthesized. It was obtained via the following series of intermediate compounds: L-acetone glycerol → D-octadecylglycerol → α-trityl-D-octadecylglycerol → α-trityl-β-hexadecanoyl-D-octadecylglycerol → β-hexadecanoyl-D-octadecylglycerol → α-octadecyl-β-hexadecanoyl-L-α-glyceryl-(2-phthalimidoethyl)phosphonate.