Tributylstannane → 6-chloro-9-[(6aR,8R,9aS)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purine

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Reaction Steps

To a solution of 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 (0.851 g, 1.28 mol) in toluene (20 mL) was added tri-n-butyltin hydride (0.680 mL, 2.53 mmol) and 2,2′-azo-bis-isobutyronitrile (0.075 g, 0.46 mmol). This solution was refluxed for 1 h. The reaction mixture was concentrated and purified by flash chromatography (0 to 50% EtOAc/hexanes) to afford the title compound (0.14 g, 74%).

Provenance & Evidence