Document Detail

A reinvestigation of the synthesis of arsonolipids (2,3-diacyloxypropylarsonic acids).
MedLine Citation:
PMID:  18313402     Owner:  NLM     Status:  MEDLINE    
A reinvestigation of the reactions leading to arsonolipids (2,3-diacyloxypropylarsonic acids) has been carried out in order to understand why the yields of their preparation were only moderate, although they are better than those reported for 2,3-diacyloxypropylphosphonic acid (phosphotidic acid). Thus, the reaction of glycidol and of 3-chloro-1,2-propanediol with alkaline sodium arsenite, "Na3AsO3", gives the desired product, 2,3-dihydroxypropylarsonic acid, and approximately 10% of an arsenic-containing glycerol dimer which is removed during the preparation of these arsonolipids. The step which is mainly responsible for the diminished yields is due to the reaction of the -As(SPh)2 or -AsO3H- precursor with the activated acid chlorides or carboxylic acid anhydrides to give an intermediate which cyclizes with the primary hydroxy group of the 2,3-dihydroxypropyl moiety. This cyclization does not allow the primary hydroxy group to be acylated. Such cyclization could not be avoided with RCOCl/py, (RCO)2O/DMAP, or RCOOH/DCC/DMAP acylating systems.
Gerasimos M Tsivgoulis; Panayiotis V Ioannou
Publication Detail:
Type:  Journal Article     Date:  2008-02-12
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  152     ISSN:  0009-3084     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  2008 Apr 
Date Detail:
Created Date:  2008-04-11     Completed Date:  2008-06-26     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  Ireland    
Other Details:
Languages:  eng     Pagination:  113-21     Citation Subset:  IM    
Department of Chemistry, University of Patras, Patras, Greece.
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MeSH Terms
Arsenicals / chemical synthesis*,  chemistry*
Arsenites / chemistry
Binding, Competitive
Carboxylic Acids / chemistry
Chemistry, Physical / methods
Chromatography, Thin Layer / methods
Glycerol / chemistry
Lipids / chemical synthesis*,  chemistry*
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Structure
Sodium Compounds / chemistry
Reg. No./Substance:
0/Arsenicals; 0/Arsenites; 0/Carboxylic Acids; 0/Lipids; 0/Sodium Compounds; 13768-07-5/sodium arsenite; 36465-76-6/arsonic acid; 56-81-5/Glycerol

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