A Novel Efficient Synthesis of Dihydroxyacetone Phosphate and Bromoacetol Phosphate for Use in Enzymatic Aldol Syntheses

Abstract

Dihydroxyacetone phosphate (DHAP, 7) and bromoacetol phosphate (BAP, 6) were synthesized in four and five steps, respectively, starting from 1,3-dibromoacetone (2). The key step involves desymetrization and ketone protection of 2 to prepare alcohol 3. Phosphorylation of 3 followed by hydrogenolysis and then deprotection of the ketal function afforded 6. A solution of 7 was prepared after treatment of 6 with NaOH. This original route allows a short and convenient preparation of DHAP in large scale and high purity for application to the synthesis of sugar derivatives and preparation of BAP for triosephosphate isomerase inhibition.