Tetrabutylammonium Fluoride → HCID 86728590, compound

Participants

Reaction Steps

To a solution of (5-(((2R,3R,4R,5S,6S)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)methoxy)pentyloxy)(tert-butyl)diphenylsilane (28, 664 mg, 0.626 mmol) from Step 1 in tetrahydrofuran (8 mL) was added tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 1.9 mL, 1.88 mmol) and the reaction mixture was stirred at ambient temperature for 2 h. After removal of organic volatiles under reduced pressure, the residue was partitioned between ethyl acetate and saturated ammonium chloride solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% tetrahydrofuran in hexanes) to yield the title compound (29, 479 mg, 0.583 mmol, 93%) as colorless oil.

Provenance & Evidence