Dibenzylphosphite → HCID 178527045, compound

Participants

Reaction Steps

A solution of 13 (0.80 g, 0.93 mmol) and 1H-tetrazole (98 mg, 1.39 mmol) in CH2Cl2 (15 mL) was treated with dibenzyldiisopropylphosphoramidite (0.43 mL, 1.39 mmol) and stirred at room temperature overnight. The product was partitioned between CH2Cl2 and H2O, dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography to give the intermediate dibenzylphosphite (0.68 g, 67%). To a solution of the dibenzylphosphite (0.39 g, 0.35 mmol) in CH3CN (5 mL) was added iodobenzenediacetate (0.17 g, 0.53 mmol). The reaction mixture was stirred at room temperature for 2 h and concentrated. The residue was partitioned between EtOAc and NaHCO3. The organic layer was washed with H2O, dried with Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel (3% 2-propanol/CH2Cl2) to give the dibenzylphosphonate (0.35 g, 88%) as a white solid.

Provenance & Evidence