反应详情

A mixture of ((R)-2-hydroxy-pent-4-enyl)-carbamic acid benzyl ester (690 mg, 2.35 mmol), osmium(VIII) oxide (4% solution in water, 0.22 mL, 35 μmol), and 4-methyl-morpholine-4-oxide (50% solution in water, 0.27 mL, 1.29 mmol) in acetone/THF/water 6:2:1 (6 mL) was stirred for 45 min at RT, then sodium metaperiodate (1.51 g, 7.04 mmol) was added, then after 16 h 10% aq. sodium sulfite solution (5.5 mL) was added. The reaction mixture was partitioned between EtOAc and water, the organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane-EtOAc gradient) produced the title compound (407 mg, 73%) as a brown gum.

1. customThe reaction mixture was partitioned between EtOAc and water
2. washthe organic layer was washed with brine
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. customevaporated