Synthesis of Benzyl Diisopropyl 5-Phosphonopentanoate and 5-Phosphonopentanoic Acid: An Analog of Succinyl Phosphate

DR Weyna, D Loveless, C Bottone, N Hifko…

Index: Weyna, David R.; Loveless, David; Bottone, Cory; Hifko, Nathan; Halkides, Christopher J. Phosphorus, Sulfur and Silicon and the Related Elements, 2007 , vol. 182, # 3 p. 563 - 567

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Abstract

Benzyl 5-(diisopropoxyphosphoryl) pentanoate (benzyl diisopropyl 5-phosphonopentanoate ) was synthesized from 5-bromopentanoic acid in three steps. The first step esterified 5- bromopentanoic acid with benzyl alcohol, the second step was a Finkelstein halogen exchange with sodium iodide, and the third step was a Michaelis–Arbuzov reaction. This compound was characterized by NMR and high-resolution mass spectrometry. This ...