تفاعل #487517

معادلة التفاعل

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

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر