反应详情

To a solution of (3S,4S,5S,2R)-5-hydroxy-5-[(phenylmethoxy)methyl]-2,3,4-tris(phenyl methoxy)cyclohexan-1-one (580.0 g, 1.051 mol) in anhydrous methylene chloride (3.6 L) was added trifluoroacetic anhydride (331.1 g, 222 mL, 1.577 mol) followed by addition of pyridine (149.7 g, 153 mL, 1.892 mol) at room temperature under argon. The mixture was stirred at room temperature for 24 h and quenched by addition of ice water (1.0 L). The organic layer was separated and the aqueous layer was extracted with methylene chloride (3×2 L). The combined organic layers were washed with sodium bicarbonate (sat. aq. 3×0.5 L), brine (sat. aq. 3×1.0 L), dried over sodium sulfate, filtered and concentrated to give a yellow oil (476.7 g, purity of 90%, yield 85%). 1H NMR (CDCl3, 400 MHz): δ 7.26-7.48 (m, 20H), 6.26 (s, 1H), 5.15 (d, J=11.2 Hz, 1H), 5.05 (d, J=10.8 Hz, 1H), 4.95 (d, J=10.8 Hz, 1H), 4.77-4.81 (m, 2H), 4.72 (d, J=11.2 Hz), 4.55 (S, 2H), 4.40-4.42 (m, 1H), 4.31 (d, J=16 Hz, 1H), 4.03-4.13 (m, 3H).

1. customquenched by addition of ice water (1.0 L)
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with methylene chloride (3×2 L)
4. washThe combined organic layers were washed with sodium bicarbonate (sat. aq. 3×0.5 L), brine (sat. aq. 3×1.0 L)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a yellow oil (476.7 g, purity of 90%, yield 85%)