反应详情

10% Palladium on charcoal (172 mg) was added to a solution of 5-[[(phenylmethoxy)carbonyl]amino]-3-(β-D-ribofuranosyl)imidazo[4,5-d][1,3]oxazin-7(1H)-one (172 mg, 0.41 mmol) in DMF (7 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 4 h. The mixture was filtered through prewashed Celite and was concentrated under high vacuum. The residue was dissolved in water and filtered through a Millipore Millex-HV filter (0.45 μm). The filtrate was lyophilized to give oxanosine as a white powder: 115 mg, (100%). Crystallization from warm water gave oxanosine (75%) as colorless needles: mp 191°-192° C.; [α]25D -38.7° (c 1, H2O); IR (KBr) 3440-3200, 1802, 1772, and 1550 cm-1 ; MS [(+) FAB]m/z 285 (M+H+); NMR (D2O) δ3.80-3.91 (m, 2), 4.21-4.23 (m, 1), 4.40 (t, 1, J=4.6 Hz), 4.69 (t, 1, J=5.5 Hz), 5.80-5.85 (d, 1, J=5.5 Hz), 7.98 (s, 1); UV max (H2O) 245 nm (ε11760), 287 (8450).

1. filtrationThe mixture was filtered through prewashed Celite
2. concentrationwas concentrated under high vacuum
3. dissolutionThe residue was dissolved in water
4. filtrationfiltered through a Millipore Millex-HV
5. filtrationfilter (0.45 μm)