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Synthesis of DL-2,3-diacyloxypropylphosphonylcholines from DL-2,3-diacyloxyiodopropanes

✍ Scribed by Paul W. Derro; Arthur F. Rosenthal; Yisrael A. Isaacson; Luis A. Vargas; Robert Bittman

Book ID: 103041382
Publisher: Elsevier Science
Year: 1976
Tongue: English
Weight: 448 KB
Volume: 16
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(76)90014-1

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✦ Synopsis

The chemical synthesis of racemic diacyloxypropylphosphonylcholines having octanoyl, myristoyl, oleoyl and stearoyl groups is described. The route involved reaction of dioactanoyloxy-, dimyristoyloxy-, dioleoyloxy-, and distearoyloxypropyliodide with tris(trimethylsilyl) phosphite to yield {he 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-, dimyristoytoxy-, dioleoyloxy-, and distearoyloxypropylphosphonylcholines. The paper also describes the synthesis of 2-octadecyleicosylphosphorylcholine.

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