Reaktion #487517

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle