反应详情

温度

100 °C

To a stirred solution of 6-[2-bromo-5-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman (300 mg, 0.363 mmol) in toluene (1.6 mL) was added tricyclohexylphosphine (10 mg), potassium phosphate (346 mg, 1.63 mmol), water (81 μl), cyclopropylboronic acid (93 mg, 1.09 mmol). The reaction mixture was degassed for 45 min then palladium (II) acetate (4 mg) was added. After heating overnight at 100° C., the reaction mixture was cooled to room temperature and was filtered through celite. The celite was washed with an additional ethyl acetate (30 mL) and the organic layer of the filtrate was separated and washed with water (20 mL) followed by brine (20 mL), then dried over sodium sulfate and concentrated to give crude product which was further purified by column chromatography to furnish 6-[2-cyclopropyl-5-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzyl]-chroman (250 mg).

1. customThe reaction mixture was degassed for 45 min
2. additionpalladium (II) acetate (4 mg) was added
3. temperaturethe reaction mixture was cooled to room temperature
4. filtrationwas filtered through celite
5. washThe celite was washed with an additional ethyl acetate (30 mL)
6. customthe organic layer of the filtrate was separated
7. washwashed with water (20 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customto give crude product which
11. customwas further purified by column chromatography