A reinvestigation of the synthesis of arsonolipids (2,3-diacyloxypropylarsonic acids) |
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Authors: | Tsivgoulis Gerasimos M Ioannou Panayiotis V |
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Affiliation: | Department of Chemistry, University of Patras, Patras, Greece. tsivgoulis@chemistry.upatras.gr |
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Abstract: | 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. |
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Keywords: | RCOOH, fatty acid RCOCl, fatty acyl chloride (RCO)2O, fatty acid anhydride RC(O)SH, thioalkanoic acid py, pyridine DMAP, 4-dimethylaminopyridine DCC, N,N′-dicyclohexylcarbodiimide DHU, 1,3-dicyclohexylurea Phosphotidic acid, 2,3-diacyloxypropylphosphonic acid Glycidol, 2,3-epoxypropanol Capric acid, decanoic acid Myristic acid, decatetranoic acid Palmitic acid, hexadecanoic acid Thiomyristic acid, thiotetradecanoic acid Thiopalmitic acid, thiohexadecanoic acid |
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