反应详情

To a solution (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (12, 4 g, 6.32 mmol) from Step 1 in methanol (90 mL) was added sodium methoxide (25% in methanol, 9 mL) and the reaction mixture was stirred at ambient temperature for 5 h. The solution was cooled to 0° C. prior to neutralizing with acetic acid (4.5 mL). After removal of organic volatiles under reduced pressure, the residue was diluted with ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with sodium hydrogen carbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound (13) as a white solid which was used without further purification.

1. temperatureThe solution was cooled to 0° C.
2. customAfter removal of organic volatiles under reduced pressure
3. additionthe residue was diluted with ethyl acetate and water
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with ethyl acetate
6. washThe combined organic layers were washed with sodium hydrogen carbonate and brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo