反应详情

To a solution of 6 (6.65 g, 10.6 mmol) in dry THF (350 mL) was added ter-butyl nitrite (6.2 mL, 52.3 mmol) and the mixture was stirred at room temperature for 1 h. Additional nitrite reagent (2.0 mL) was added and the mixture was stirred at 50°-60° C. overnight. The mixture was evaporated and the residue was purified by flash column chromatography on silica gel using 8-10% acetone in CH2Cl2 followed by 10-11%. The desired product eluted last to yield 3.45 g (46%) of 9 as a foam: UV λmax (EtOH) 220 nm (ε46600), 259 sh (11000), 271 sh (8400): 1H NMR (DMSO-d6) δ6.31 (d, J=6.45 Hz, 1H, C1, H), 7.38-7.98 (m, 15H, benzoyl aromatics), 8.25 (s, 1H, C5H), 13.16 (b, 1H, N6H, exchanged with D2O), and other sugar protons. Anal. Calcd. for C31H23N3O9 :

1. stirringthe mixture was stirred at 50°-60° C. overnight
2. customThe mixture was evaporated
3. customthe residue was purified by flash column chromatography on silica gel using 8-10% acetone in CH2Cl2
4. washThe desired product eluted last