An improved synthesis of phosphonomethyl analogues of glyceraldehyde-3-phosphate and dihydroxy-acetone phosphate

Article abstract of DOI:10.1016/0040-4039(95)01678-B

Compounds 1 and 2, phosphonate analogues of dihydroxy-acetone phosphate (DHAP) and glyceraldehyde-3-phosphate (GAP) respectively, are easily and quantitatively obtained from diethyl-4,4-diethoxy-3-hydroxybutyl-1-phosphonate 3. Depending upon the acidic conditions utilised for the deprotection of the phosphonate and carbonyl groups, the aldol/ketol rearrangement allows the synthesis of either compound.