反应详情

To a solution of the (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)naphthalen-1-yl)-tetrahydro-2H-pyran in EtOH (80 mL) and water (40 mL) was added potassium cyanide (4.24 g, 65.1 mmol). The reaction mixture was refluxed overnight. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The crude residue was purified by column chromatography to yield 2-(4-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxy-methyl)-tetrahydro-2H-pyran-2-yl)naphthalen-2-yl)acetonitrile (10.9 g, 46%) as a white solid.

1. temperatureThe reaction mixture was refluxed overnight
2. extractionextracted with EtOAc
3. washThe organic layer was washed with brine
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. customevaporated in vacuo
7. customThe crude residue was purified by column chromatography