Phenyl thioxochloroformate → O-[(6aR,8R,9S,9aR)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-yl] O-phenyl thiocarbonate

Participants

Reaction Steps

To a solution of (6aR,8R,9S,9aR)-8-(6-chloro-9H-purin-9-yl)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-9-ol (0.762 g, 1.44 mmol) and N,N-dimethylaminopyridine (0.529 g, 4.34 mmol) in DCM (20 mL) was added phenyl chlorothionocarbonate (0.440 mL, 3.2 mmol) and the solution was stirred for 1 h. The reaction mixture was concentrated and the residue purified by flash chromatography (0 to 50% EtOAc/hexanes) to afford the title compound (0.851 g, 88%).

Provenance & Evidence