反应详情

Treat a mixture of (R)-4-benzyl-3-[(S)2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one (0.96 g, 1.8 mmol), THF (21 mL) and water (7 mL) with 2.5% osmium tetroxide in t-butanol (46 mg, 0.18 mmol). Add sodium periodate (1.17 g, 5.5 mmol) and stir the reaction 4 hr at room temperature. Quench the reaction with water and extract with ethyl acetate. Wash the organic phase with aqueous 1N sodium thiosulfate then brine. Dry the organic layer over magnesium sulfate, filter, and concentrate under vacuum. Purify the crude material by silica gel chromatography using hexanes:ethyl acetate to elute the pure product. Concentrate the fractions containing product under vacuum to afford 0.46 g (48%) of desired product. MS (m/z): 526 (M+).

1. additionTreat
2. customthe reaction 4 hr at room temperature
3. customQuench
4. customthe reaction with water
5. extractionextract with ethyl acetate
6. washWash the organic phase with aqueous 1N sodium thiosulfate
7. dry with materialDry the organic layer over magnesium sulfate
8. filtrationfilter
9. concentrationconcentrate under vacuum
10. customPurify the crude material by silica gel chromatography
11. washethyl acetate to elute the pure product
12. concentrationConcentrate the fractions
13. additioncontaining product under vacuum