Acetic Acid → HCID 86714025, compound

Participants

Reaction Steps

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.

Provenance & Evidence