Bis-ketol phosphate alkyl triesters: Rate of initial ketol group hydrolysis

Article abstract of DOI:10.1016/0040-4039(95)02402-6

Bis-(2-oxo-2-phenyl ethyl) tetrahydrofurfuryl phosphate (7) was synthesized by the addition of tetrahydrofurfuryl alcohol to the corresponding bis-ketol hydrogen phosphate (8) using DCC as the condensing agent. The rate of loss of a single ketol group was determined over the pH range 6.9 to 9 and at different temperatures. At pH 7.4 and 37°C compound 7 hydrolyzed with a pseudo-first rate constant of 6.2 x 10^-4 s^-1. This hydrolysis rate is 10⁸ fold faster than a simple alkyl phosphate triester. The rate of hydrolysis is similar to that observed for mono-ketol dialkyl phosphate triesters.