反应详情

温度

-78 °C

To a solution of 4-bromo-1-chloro-2-(4-vinylbenzyl)benzene (intermediate AM) (215 mg) in toluene:THF (2:1) (3 mL) at −78° C. was added n-BuLi (0.34 mL, 2.5 M in hexane) dropwise. After 45 min, the above mixture was added dropwise into a pre-cooled (−78° C.) solution of (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxylmethyl)tetrahydro-2H-pyran-2-one (453 mg) in toluene (3 mL). After being stirred for 2.5 h at −78° C., the reaction mixture was quenched by saturated NH4Cl and diluted with ethyl acetate. The organic layer was separated, washed with brine and dried over Na2SO4. Concentration gave the crude product which was purified by chromatography to provide intermediate AN (712 mg) as an oil.

1. additionthe above mixture was added dropwise into
2. customthe reaction mixture was quenched by saturated NH4Cl
3. additiondiluted with ethyl acetate
4. customThe organic layer was separated
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. concentrationConcentration