Isosteres of natural phosphates. 4. The synthesis of phosphonic acid analogues of phosphatidic acid and acyldihydroxyacetone phosphate

Abstract

The chemical synthesis of 3,4-diacyloxybutyl-1-phosphonic acids having palmitoyl and oleoyl groups is described. These were prepared by reaction of the appropriate 3,4-diacyloxybutyl-1-bromide with tris (trimethylsilyl) phosphite followed by mild hydrolysis of the trimethylsilyl groups from the phosphonic acid. Also reported is the preparation of 4-palmitoyl-3-oxobutyl-1-phosphonic acid by the acylation of 4-hydroxy-3-oxobutyl-1-phosphonic acid. This latter compounds is an isosteric analogue of acyldihydroxyacetone phosphate.