反应详情

温度

20 °C

A solution of 9-(1-t-butyldimethylsilyloxy-3-diethoxyphosphorylmethoxyprop-2-oxy)-6-chloro-2-formamidopurine (280 mg, 0.51 mmol) in 80% aqueous formic acid (5 ml) was stirred at 120° C. for 3 hours. The acid was evaporated, the residue dissolved in methanol (1 ml) and 0.88 ammonia (1 ml) and stirred for 1 hour at 20° C. After evaporation, the residue was dissolved in hot water (5 ml) and extracted with ether (3×5 ml). The aqueous solution was passed down a reverse-phase silica column eluting with up to 15% methanol affording 9-(1-diethoxyphosphorylmethoxy-3-hydroxyprop-2-oxy)guanine (105 mg, 53%) m.p. 238°-240° C. νmax (KBr) 3380, 1700, 1600, 1380, 1380, 1240, 1030 and 960 cm-1 ; δH [(CD3)2SO] 1.24(6H, t, J7.2 Hz, 2×(CH2CH3 ), 3.61(2H, t, J5.2 Hz, CH2OH), 3.81(2H, d, J4.7 Hz, CH2OCH2P), 3.89(2H. d, J8.0 Hz,CH2P), 4.04 (4H, m, 2×CH2CH3, 4.39(1H, t, J4.7 Hz,CHON), 5.06(1H, t, J6.0 Hz, D2O exchangeable, OH), 6.61(2H, br.s, D2O exchangeable, NH2), 7.86(1H, s, H-8), 10.67(1H, br.s, D2O exchangeable, NH); m/z (FAB+veIon), 392(MH+, 2%), 414(MNa+, 100%). Found: C,39.27; H,5.60; N,17.78%; C13H22N5O7P.0.3H2O requires C,39.36; H,5.74; N,17.66%.

1. customThe acid was evaporated
2. dissolutionthe residue dissolved in methanol (1 ml)
3. customAfter evaporation
4. dissolutionthe residue was dissolved in hot water (5 ml)
5. extractionextracted with ether (3×5 ml)
6. washeluting with up to 15% methanol