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Synthesis of lipid-based unsymmetrical O,O-dialkylphosphites

Abstract : An efficient method for the synthesis of unsymmetrical lipid-based O,O-dialkylphosphites is reported. The reaction implies the use of H-phosphonates monoester ammonium salt which is coupled with a fatty alcohol in the presence of an optimized quantity of pivaloyl chloride (Piv-Cl) as coupling reagent. The reaction conditions offer access to a wide panel of unsymmetrical O,O-dialkylphosphites including either non-functionalized lipid derivatives (lauryl, dodecyl tetradecyl, hexadecyl, octadecyl), ramified lipid (phytanyl), unsaturated lipids (oleyl, linoleyl) or ω-functionalized alkyl alcohols (azide, propargyl, alkenyl).
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Submitted on : Friday, June 16, 2017 - 3:41:59 PM
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Mathieu Berchel, Jimmy Haddad, Stéphanie Le Corre, Jean-Pierre Haelters, Paul-Alain Jaffres. Synthesis of lipid-based unsymmetrical O,O-dialkylphosphites. Tetrahedron Letters, 2015, 56 (18), pp.2345 - 2348. ⟨10.1016/j.tetlet.2015.03.093⟩. ⟨hal-01540799⟩



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