Réaction #487517

Équation de réaction

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

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreSolvents were removed under the reduced pressure
2. 2
   workup.DISSOLUTIONthe resulting residue was dissolved in dichloromethane (50 mL)
3. 3
   Lavagewashed with water, saturated ammonia chloride, brine
4. 4
   Séchagedried over sodium sulfate
5. 5
   Concentrationconcentrated
6. 6
   AutreThe residue was purified by silica gel chromatography
7. 7
   Lavageeluting with 1:1 hexane-ethyl acetate
8. 8
   Autreto give V (640 mg, 85%) as a white foam

Mode opératoire

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.

Source