反应详情

温度

35 °C

1-Hydroxypyridine-2(1H)-one (1, 0.50 g, 4.5 mmol) was dissolved in 10 mL of dichloromethane. To this was added 1-bromo-α-D-glucose tetraacetate (0.74 g, 1.8 mmol) and tetrabutylammonium bromide (0.58 g, 1.8 mmol). After heating to 35° C., 10 mL of 1.0 M NaOH was added. The heterogeneous reaction mixture was vigorously stirred for 3 h. After cooling to room temperature, the reaction was diluted with 20 mL of ethyl acetate then washed 2× with 1.0 M NaOH (20 mL) followed by water and brine. The organic layer was dried over MgSO4, filtered, and concentrated for silica gel column purification in 2% MeOH in CH2Cl2 yielding an off-white solid in 29% yield (0.23 g). 1H NMR (500 MHz, CDCl3) δ=7.51 (dd, J1=6.9 Hz, J2=1.8 Hz, 1H), 7.28 (dt, J1=8.6 Hz, J2=2.9 Hz, 1H), 6.60 (dd, J1=9.8 Hz, J2=1.8 Hz, 1H), 6.04 (dt, J1=6.9 Hz, J2=1.7 Hz, 1H), 5.29 (t, J=9.2 Hz, 1H), 5.21 (d, J=8.6 Hz, 1H), 5.16 (t, J=9.8 Hz, 1H), 5.09 (t, J=9.8 Hz, 1H), 4.26 (dd, J1=12.6 Hz, J2=5.2 Hz, 1H, CHCHaHbOAc), 4.09 (dd, J1=12.1H, J2=2.3 Hz, 1H, CHCHaHbOAc), 3.68 (dq, J1=10.3 Hz, J2=2.3 Hz, 1H, CHCHaHbOAc), 2.16 (s, 3H), 2.02 (s, 3H), 2.00 (s, 6H). 13C NMR (125 MHz, CDCl3) δ=170.5, 170.1, 169.9, 169.5, 157.9, 139.3, 137.8, 122.8, 104.3, 103.5, 77.5, 72.3, 69.3, 68.0, 61.4, 20.7. ESI-MS(+): m/z 441.77[M+H]+, 464.06[M+Na]+.

1. temperatureAfter cooling to room temperature
2. washthen washed 2× with 1.0 M NaOH (20 mL)
3. dry with materialThe organic layer was dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated for silica gel column purification in 2% MeOH in CH2Cl2 yielding an off-white solid in 29% yield (0.23 g)