反应 #487517

反应方程式

1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose

benzylamine

→

2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose

溶剂

THF

反应条件

后处理

1. 1
   其他Solvents were removed under the reduced pressure
2. 2
   workup.DISSOLUTIONthe resulting residue was dissolved in dichloromethane (50 mL)
3. 3
   洗涤washed with water, saturated ammonia chloride, brine
4. 4
   干燥dried over sodium sulfate
5. 5
   浓缩concentrated
6. 6
   其他The residue was purified by silica gel chromatography
7. 7
   洗涤eluting with 1:1 hexane-ethyl acetate
8. 8
   其他to give V (640 mg, 85%) as a white foam

实验过程

To a solution of 1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose (IV, 850 mg, 2.78 mmol) in THF (12 mL) was added benzylamine (0.23 mL) and the mixture was stirred at rt overnight. Solvents were removed under the reduced pressure and the resulting residue was dissolved in dichloromethane (50 mL) and washed with water, saturated ammonia chloride, brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with 1:1 hexane-ethyl acetate, to give V (640 mg, 85%) as a white foam. 1H NMR (500.1 MHz) (CD3Cl) δ: 5.50 (m, 2H), 5.03 (t, J=10.5 Hz, 1H), 4.90 (m, 1H), 4.24 (m, 1H), 3.35 (m, 2H), 2.12 (s, 3H), 2.05 (s, 3H), 2.02 (s, 3H). 13C NMR (125.8 MHz) (CDCl3) δ: 170.26, 170.23, 169.78, 89.98, 71.09, 69.71, 68.34, 51.05, 20.68, 20.62, 20.58.

来源