Benzaldehyde → (2R,3R,4S,5R)-2-[2-[(Benzylamino)methyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

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Reaction Steps

(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (110 mg, 0.22 mmol) was dissolved (using gentle heating) in dry tetrahydrofuran (15 ml). The stirred solution was then cooled to room temperature and treated with a solution of benzaldehyde (21 mg, 0.20 mmol) in dry tetrahydrofuran (2 ml) followed by addition of sodium triacetoxyborohydride (70 mg, 0.33 mmol). The resultant mixture was stirred at room temperature for 24 hr, diluted with ethyl acetate and then washed sequentially with saturated aqueous sodium hydrogen carbonate and brine. The organic solution was then dried with anhydrous magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (92:8) to afford the title compound as a solid (67 mg). MS: 581 (MH+).

Provenance & Evidence