Synthesis of DL-2,3-diacyloxypropylphosphonyl-cholines from DL-2,3-diacyloxyiodopropanes.
The chemical synthesis of racemic diacyloxypropylphosphonylcholines having octanoyl, myristoyl, oleoyl and stearoyl groups is described. The route involved reaction of dioactanoyloxy-dimyristoyloxy-dioleoyloxy-, and distearoyloxpropyliodide with tris (trimethylsilyl) phosphite to yield the corresponding bis (trimethylsilyl) phosphonate. Removal of the trimethylsilyl groups by neutral aqueous hydrolysis gave the free diacylpropylphosphonic acids, which, when treated with choline toluenesulfonate, yielded the desired dioctanoyloxy-, dimyristoyloxy-, dioleoyloxy-, and distearoyloxypropylphosphonylcholines. The paper also describes the synthesis of 2-octadecyleicosylphosphorylcholine.
D002855:Chromatography, Thin Layer; D008722:Methods; D063065:Organophosphonates / Q000138:chemical synthesis; D010743:Phospholipids / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared
D063065:Organophosphonates; D010743:Phospholipids