Azobisisobutyronitrile → N1,5'-O-dibenzyl-2',3'-didehydro-2',3'-dideoxyinosine

Participants

Reaction Conditions

Reaction Steps

An acetonitrile solution (1 mL) of N1,5′-O-dibenzyl-2′,3′-bis-O-[(methylthio)thiocarbonyl]inosine (314 mg, 0.5 mmol) was heated to 80° C. To this solution, an acetonitrile solution (1 mL) of N-ethylpiperidine hypophosphite (358 mg, 2 mmol) and 2,2′-azobisisobutyronitrile (16.4 mg, 0.1 mmol) were added, and the mixture was then stirred at 90° C. for one hour. After the reaction mixture was cooled, the reaction was terminated with the addition of water (3 mL). The reaction mixture was extracted by the addition of ethyl acetate (15 mL), and the resultant organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. After purification by chromatography (using 12 g of silica gel and a mixed solvent of hexane and ethyl acetate (1:2) as an eluting solution), 150 mg of the intended product was obtained in a yield of 71% as a colorless oily material.

Provenance & Evidence