反应详情

To a stirred solution of 1-deoxynojirimycin (100 g, 0.61 mol) in saturated aqueous sodium bicarbonate (1000 ml), benzyl chloroformate (95%, 121 g, 0.67 mol) was added dropwise at room temperature. After stirring at room temperature for 18 hr, the solution was extracted once with methylene chloride (300 ml) to remove any unreacted benzyl chloroformate. The aqueous layer was then extracted several times with ethyl acetate to give a total of 2.5-3 liters of the extract. The organic layer was then dried (Na2SO4), filtered and concentrated to give (2) a white solid (98 57 g, 54%), mp 101°-2° C., Anal calcd. for C14H19NO6C, 56.56, H, 6.44, N, 4.71 Found C, 56.33, H, 6.38, N, 4.58., 1H NMR (CD3OD) 7.2-7.4 (m, 5H), 5.15 (s, 2H), 4.23 (br m, 1H), 4.05 (br d., J=8 Hz, 1H), 3.87 (dd, J=6, 4 Hz, 1H), 3.78-3.85 (m, 2H), 3.70-3.78 (m, 2H), 3.45 (br d, J=8 Hz, 1H).

1. extractionthe solution was extracted once with methylene chloride (300 ml)
2. customto remove any unreacted benzyl chloroformate
3. extractionThe aqueous layer was then extracted several times with ethyl acetate
4. customto give a total of 2.5-3 liters of the extract
5. dry with materialThe organic layer was then dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated