反应详情

温度

45 °C

To a solution of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 1j (8.53 g, 12.08 mmol) in dichloromethane (350 mL) was added 2-iodoxybenzoicacid (6.77 g, 24.2 mmol) at room temperature. The mixture was refluxed at 45° C. for 36 hours and quenched with 150 mL of water. The mixture was partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium chloride (150 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 1k as pale yellow oil (4.94 g, 60.0%).

1. customquenched with 150 mL of water
2. customThe mixture was partitioned between dichloromethane and water
3. washThe organic layer was washed with saturated aqueous sodium chloride (150 mL×2)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica gel chromatography
7. washeluted with PE/EtOAc(v/v)=10/1