(S)-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]adenine → (S)-9-[2-(diethoxyphosphorylmethoxy)3-hydroxypropoxy]adenine

Participants

Reaction Steps

10% Pd-C (50 mg) was added to a solution of (S)-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]adenine (0.21 g, 0.45 mmol) in dichloromethane (5 ml) and trifluoroacetic acid (lml) and the mixture hydrogenated at atmospheric pressure and ambient temperature for 5 hours. The mixture was filtered, the filtrate evaporated and the residue obtained dissolved in ethanolic ammonia solution (5 ml). After 15 minutes the solvent was evaporated and the residue chromatographed on silica gel using dichloromethane/methanol 90:10 as eluant. T.l.c. examination of the product indicated traces of a non UV absorbing impurity which was removed by prep. t.l.c. using dichloromethane/methanol 88:12 as eluant. (S)-9-[2-(diethoxyphosphorylmethoxy)3-hydroxypropoxy]adenine was obtained as a colourless gum (0.11 g, 65%). 1H NMR: δH [(CD3)2SO] 1.23 (6H, t, J=7 Hz, (OCH2CH3)2), 3.5-3.65 (2H, m, CH2OH), 3.75-3.85 (1H, m, CH), 3.98-4.15 (6H, m, OCH2P, (OCH2CH3)2), 4.38 (1H, dd, J=6.6 Hz, J=11.3 Hz, NOCHB), 4.54 (1H, dd, J=3 Hz, J=11.3 Hz, NOCHA), 4.88 (1H, t, J=5.5 Hz, D2O exchangeable OH), 7.38 (2H, br.s, D2O exchangeable NH2), 8.15 (1H, s, H-2 or H-8), 8.43 (1H, s, H-2 or H-8). m/z: (FAB+, thioglycerol matrix) 376 (MH+).

Provenance & Evidence