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

Add time:08/01/2019    Source:sciencedirect.com

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 × 10−4s−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.

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