Hydrogen Peroxide → 8-trifluoromethyl-2',3',5'-tri-O-acetylguanosine

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Reaction Conditions

Reaction Steps

0.41 g (1.0 mmol) of 2′,3′,5′-tri-O-acetylguanosine was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l of dimethyl sulfoxide solution of trifluoromethyl iodide, 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 8-trifluoromethyl-2′,3′,5′-tri-O-acetylguanosine (19F-NMR yield: 51%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 8-Trifluoromethyl-2′,3′,5′-tri-O-acetylguanosine was obtained as a yellow solid (0.22 g, yield: 47%) by silica gel column chromatography.

Provenance & Evidence