Triphenylphosphine → (3R,3aR,6R,6aS)-6-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)thio)hexahydrofuro[3,2-b]furan-3-ol

Participants

Reaction Steps

Triphenylphosphine (34.1 mg, 0.130 mmol) and DEAD (0.021 ml, 0.130 mmol) were added to a stirred mixture of 5-([1,1′-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine-2-thiol (30.4 mg, 0.065 mmol) and (3S,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (25.4 mg, 0.097 mmol) in THF (1 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by preparative TLC, eluting with EtOAc/isohexane (2:8) to give the title compound. LC-MS: calculated for C36H48ClN3O4SSi2 709.26 observed m/e: 710.42 (M+H)+ (Rt 1.59/2 min);

Provenance & Evidence