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A facile synthesis of 1-O-alkyl-2-(R)-hydroxypropane-3-phosphonocholine (lyso-phosphono-platelet activating factor).

Publication ,  Journal Article
Schmitt, JD; Nixon, AB; Emilsson, A; Daniel, LW; Wykle, RL
Published in: Chem Phys Lipids
October 1992

The synthesis of 1-O-alkyl-2-(R)-hydroxypropane-3-phosphonocholine is described. An efficient alkylation procedure using (NaH/DMSO) catalysis is also described and applied to the synthetic scheme. The key intermediate 1-O-alkyl-2-(R)-O-benzyl-3-bromopropane was phosphonylated using tris(methylsilyl)phosphite; the resulting phosphonic acid was coupled to choline using trichloroacetonitrile/pyridine or triisopropylbenzenesulfonyl chloride/pyridine followed by catalytic hydrogenation to yield 1-O-alkyl-2(R)-hydroxypropane-3-phosphonocholine.

Duke Scholars

Published In

Chem Phys Lipids

DOI

ISSN

0009-3084

Publication Date

October 1992

Volume

62

Issue

3

Start / End Page

263 / 268

Location

Ireland

Related Subject Headings

  • Type C Phospholipases
  • Substrate Specificity
  • Platelet Activating Factor
  • Phospholipase D
  • Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Indicators and Reagents
  • Biophysics
  • 3205 Medical biochemistry and metabolomics
  • 3101 Biochemistry and cell biology
 

Citation

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MLA
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Schmitt, J. D., Nixon, A. B., Emilsson, A., Daniel, L. W., & Wykle, R. L. (1992). A facile synthesis of 1-O-alkyl-2-(R)-hydroxypropane-3-phosphonocholine (lyso-phosphono-platelet activating factor). Chem Phys Lipids, 62(3), 263–268. https://doi.org/10.1016/0009-3084(92)90063-u
Journal cover image

Published In

Chem Phys Lipids

DOI

ISSN

0009-3084

Publication Date

October 1992

Volume

62

Issue

3

Start / End Page

263 / 268

Location

Ireland

Related Subject Headings

  • Type C Phospholipases
  • Substrate Specificity
  • Platelet Activating Factor
  • Phospholipase D
  • Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Indicators and Reagents
  • Biophysics
  • 3205 Medical biochemistry and metabolomics
  • 3101 Biochemistry and cell biology