Abstract The synthesis of all four deoxyfluoro-α-d-glucopyranosyl phosphates is described. Rate constants for their acid-catalyzed hydrolysis were determined, and fluorine substitution was shown to have a significant effect in lowering the rate, particularly when the substitution is adjacent to the anomeric center. Relative rate-constants measured in m HClO 4 at 25 are 60.30: 1.00: 7.05: 3.97: 16.5 for α-d-glucopyranosyl phosphate and the 2-, 3-, 4-and 6- ...
