Triphenylphosphine → HCID 54131397, compound

Participants

Reaction Steps

N6 -Benzoyl-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine (7.0 g, 15.3 mmol), triphenylphosphine (6.0 g, 22.9 mmol), and LiN3 (2.8 g, 56.4 mmol) were dissolved in DMF (100 mL). To this stirring mixture was added diethylazodicarboxylate (3.6 mL, 22.9 mmol) in one portion, the reaction was stirred for 2.5 h at RT, and the reaction was quenched with H2O (10 mL). The solvents were removed in vacuo, the residual oil was redissolved in EtOAc (300 mL) and extracted with H2O (2×200 mL) and saturated. aq. NaCl (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residual oil was purified on SiO2 (2-5% MeOH/CH2 Cl2) to afford 5'-O-Benzoyl-N6 -benzoyl-3'-azido-2',3'-dideoxyadenosine, 1a, as an amber foam, which was taken on directly to hydrogenation.

Provenance & Evidence