Isosteres of natural phosphates. 4. The synthesis of phosphonic acid analogues of phosphatidic acid and acyldihydroxy acetone phosphate.
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 trimethyl-silyl 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 compound is an isosteric analogue of acyldihydroxyacetone phosphate.
D002855:Chromatography, Thin Layer; D004099:Dihydroxyacetone Phosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D063065:Organophosphonates / Q000138:chemical synthesis; D010712:Phosphatidic Acids / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014306:Trioses / Q000031:analogs & derivatives*
D063065:Organophosphonates; D010712:Phosphatidic Acids; D014306:Trioses; D004099:Dihydroxyacetone Phosphate