反应详情

Compound 8 (5.2 g, 19.53 mmol) in saturated NH3 in MeOH (150 mL) was kept at room temperature for 9 h. After evaporation, the residue was dissolved in DMF (60 mL). To this were added imidazole (5.32 g, 78.12 mmol) and tert-butyldimethylsilyl chloride (8.83 g, 58.59 mmol) at 0° C. The reaction mixture was stirred at room temperature for 11 h, and then partitioned between EtOAc/H2O (250 mL/50 mL×4). Silica gel column chromatography (hexane/EtOAc=10/1) of the organic layer gave 9 (6.43 g, 97%) as a foam: UV (MeOH) λmax 266 nm (ε11600), λmin 236 nm (ε5700); 1H NMR (CDCl3) δ 0.11 and 0.14 (6H, each as s, SiMe), 0.88 (9H, s, SiBu-t), 1.92 (3H, d, J6,CH3=1.2 Hz, Me), 2.03 (1H, dt, Jgem=10.8 Hz, J1′,2′a=3.2 Hz and J2′a,3′=3.2 Hz, H-2′a), 2.61-2.68 (1H, m, H-2′b), 4.25 (1H, d, Jgem=2.2 Hz, H-5′a), 4.57 (1H, d, Jgem=2.2 Hz, H-5′b), 4.68 (1H, dd, J2′a,3′=3.2 Hz, J2′b,3′=6.8 Hz H-3′), 6.46 (1H, dd, J1′,2′a=3.2 Hz and J1′,2′b=7.2 Hz, H-1′), 7.44 (1H, d, J6,CH3=1.2 Hz, H-6), 9.12 (1H, br, NH); FAB-MS m/z 339(M++H). Anal. Calcd for C16H26N2O4Si: C, 56.78; H, 7.74; N, 8.28. Found: C, 56.61; H, 7.87; N, 8.17.

1. customAfter evaporation
2. dissolutionthe residue was dissolved in DMF (60 mL)
3. custompartitioned between EtOAc/H2O (250 mL/50 mL×4)