Tributylstannane → HCID 86651443, compound

Participants

Reaction Steps

To a solution of 1-(2-deoxy-5-O-trityl-β-D-ribofuranosyl)-4-(1-propynyl)pyrrole-2-carbaldehyde (392 mg, 797 μmol) in acetonitrile were added 4-dimethylaminopyridine (975 mg, 7.98 mmol) and phenyl chlorothioformate (470 μl, 3.40 mmol) in an argon atmosphere, and the reaction mixture was stirred at room temperature. After 23 hours, the reaction solution was concentrated under reduced pressure, and purified by column chromatography on silica gel (50-67% CH2Cl2 in hexane) to give an intermediate (193 mg, containing minor amounts of impurities). To a solution of this intermediate in toluene (10 ml) were added tri-n-butyltin hydride (165 μl, 612 μmol) and α,α′-azobisisobutyronitrile (15 mg, 92 μmol), and the reaction mixture was refluxed for 5 hours in an argon atmosphere. The reaction solution was concentrated under reduced pressure, and the resulting crude product was purified by column chromatography on silica gel (eluent: 50-80% CH2Cl2 in hexane) to give the title product (84 mg, 58%).

Provenance & Evidence