2-Deoxy-2-fluoro-neo-inositol

Analogues of myo-lnositol were synthesized wherein certain hydroxyl groups were replaced with fluorine, and these were examined as substrates for phosphatidylinositol (Pl) synthetase. Fluorine substitution at the 2- and 4(6)-p03itions of myo-inositol (giving the acyllo- and myo-iaomers, respectively) resulted in loss of any detectable substrate activity. Replacement of the hydroxyl at C-5 of myo-inosltol resulted in retention of appreciable PI synthetase activity (ca. 2S% for the equatorial 5-deoxy-5-fluoro-myo- and ca. 1 (>% for the axially substituted 2-deoxy-2-fluoro-neo-inositol). 

Figure 2. Target Deoxyfluorocyclitols 1 -Deo3cy-1 -fluoro-scyllo-inositol (2) 4(6)-Deoxy-4(6)-fluoro-myo-inositol (3) 5-Deoxy-5-fluoro-myo-inositol (4) 2-Deoxy-2-fluoro-neo-inositol (5) 5-Deoxy-5,5-dif luoro-myo-inosi to 1 (6).

Deoxy-5-fluoro-myo-inositol (4) and 2-deoxy-2-fluoro-neo-inositol... 

Figure 4. Synthesis of 5-deoiy-5-fluoro-myo-inositol (4) and 2-deoxy-2-fluoro-neo-inositol (5). Reagents a. Diethylaminosulfur trifluoride (dAST) b. H2 - Pd(0H)2/C, HO Ac c. AC2O - pyridine.

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