Tetrabutylammonium Fluoride → (2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{2-[(1-ethylpropyl)amino]ethyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol

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Reaction Steps

N-(2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}ethyl)-N-(1-ethylpropyl)amine (250 mg, 0.31 mmol) (preparation 19) was dissolved in dry tetrahydrofuran (1 ml), a 1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1 ml, 1 mmol) added and the mixture stirred at room temperature for 3 days. The solvent was removed under reduced pressure and the residue purified by column chromatography eluting with a gradient system of dichloromethane:methanol:ammonia (94:6:0.6) changing to dichloromethane:methanol:ammonia (90:10:1) to give the crude product as a foam. This was dissolved in ethyl acetate (15 ml) and the solution washed sequentially with dilute aqueous sodium hydroxide solution, brine and water, then dried with anhydrous sodium sulfate. The solvent removed under reduced pressure to give the title compound as a powder (100 mg). MS: 575 (MH+)

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