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Phosphono-platelet activating factor. II. Synthesis of 2-acetamido-2-deoxy-1-O-octadecylglycerol-3-(2-trimethylammoniumethyl) and (2-aminoethyl)phosphonates

✍ Scribed by Michael C. Moschidis; Constantin A. Demopoulos

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 306 KB
Volume: 37
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(85)90073-8

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✦ Synopsis

The chemical synthesis of the amide analogs of 1-O-alkyl-2-O-acet yl-glyceryl-3-O-phosphoryl cholinc as its phosphono analog (phosphono-AGEPC)and 1-O-alkyl-2-O-acetyl-glyceryl-3-Ophosphoryl ethanolamine as its phosphono analog (phosphono-AGEPE) is reported.

The intermediate acetamides for the subsequent phosphonylations were obtained (i) by classical organic reactions and (it) by the method of Chandrakumar and ftadju (Tetrahedron Lett., 23 (1982) 1043-1046). Phosphonylation for the choline analog was accomplished with 2-bromoethyl phosphonic acid monochloride in anhydrous and ethanol-free chloroform in the presence of triethyhmine. This was followed by reaction with anhydrous trimethylamine in dimethylformamide in a sealed tube at 50-55°C for 3 days.

Phosphonylation for the ethanolamine analog was accomplished with 2-phthalimidoethylphosphonic acid monochloride in anhydrous and ethanol-free chloroform in the presence of anhydrous triethylamine, followed by hydrazinolysis in 90% ethanol under reflux for 4 h. The products were identified by elemental analysis, thin-layer chromatography (TLC) and IR spect ro scopy.

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