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.
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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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ICMJE
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
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