반응 #487516

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

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

sulfuric acid

acetic acid

→

IV

수율 82.0%

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

수율 82.0%

용매

acetic anhydride

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후처리

1. 1
   추출Extraction with dichloromethane (3×50 mL)
2. 2
   세척washed with water, saturated sodium bicarbonate, brine
3. 3
   건조dried over sodium sulfate
4. 4
   농축concentrated
5. 5
   기타The residue was purified by silica gel chromatography
6. 6
   세척eluting with 1:1 hexane-ethyl acetate

실험 절차

To a solution of methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranoside (III, 1.0 g, 2.9 mmol) in acetic acid (20 mL) and acetic anhydride (20 mL) at 0° C. was added sulfuric acid (97%, 1 mL) and the mixture was stirred at rt for 20 hr and then poured into ice (100 g). Extraction with dichloromethane (3×50 mL) and washed with water, saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with 1:1 hexane-ethyl acetate, to give IV (886 mg, 82%) as a white foam. 1H NMR (500.1 MHz) (CD3Cl) δ: 6.28 (d, J=4.0 Hz, 1H), 5.41 (t, J=9.5 Hz, 1H), 5.03 (m, 2H), 4.03 (m, 1H), 3.24-3.37 (m, 2H), 2.13 (s, 3H), 2.04 (s, 3H), 1.99 (s, 3H), 1.95 (s, 3H). 13C NMR (125.8 MHz) (CDCl3) δ: 170.11, 169.53, 169.33, 168.62, 88.78, 70.83, 69.58, 69.08, 68.94, 50.61, 20.75, 20.55, 20.46, 20.34.

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