反应详情

To a solution of swainsonine acetonide (104 mg, 0.49 mmol) in THF (6.5 ml) was added 6.0 ml of 6M HCl. The colorless solution was stirred overnight at room temperature. The solvent was removed in vacuo, leaving a colorless, viscous oil. The oil was then purified by an ion exchange chromatography (Dowex-1×8). Fractions (visualized with iodine or ninhydrin) were collected and concentrated in vacuo to furnish 68.5 mg(81% yield) of swainsonine as a white solid: mp and mixed mp 140-142 C; [ ]D25 =-75.71 (c 2.33, MEOW); Rf=0.36 in 1-butanol:chloroform:ethanol:concentrated ammonium hydroxide (4:4:4:1); 1H NMR (D2O, ref. DSS, 300 MHz ) 4.34 (m, 1H, B-2), 4.24 (dd, J1,8a =3.7 Hz, J1,2 =6.1 Hz, 1H, H-1), 3.78 (ddd, J=3.9, 9.3 & 10.7 Hz, 1H, H-8), 2.89 (m, 1H), 2.86 (dd, J=2.6 & 11.0 Hz, 1H, H-3), 2.53 (dd, J=7.8 & 11.0 Hz, 1H, H-3'), 2.04 (m, 1H), 1.96 (m, 1H), 1.89 (dd, J8a,8 =9.3 Hz, J8a,1 =3.7 Hz, H-8a), 1.70 (m, 1H), 1.49 (m, 1H), 1.22 (m, 1H); 13C NMR (D2O, ref: CH3CN, 100 MHz) δ23.21, 32.51, 51.72, 60.65, 66.37, 69.08, 69.72, 72.87; HRMS(M+) 173.1052 calcd for C8H15NO3, found 173.1041.

1. customThe solvent was removed in vacuo
2. customleaving a colorless, viscous oil
3. customThe oil was then purified by an ion exchange chromatography (Dowex-1×8)
4. customFractions (visualized with iodine or ninhydrin) were collected
5. concentrationconcentrated in vacuo