반응 #487517

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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

용매

THF

반응 조건

후처리

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

실험 절차

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.

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