Sodium borohydride → HCID 71117151, 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)pentan-1-ol (29, 479 mg, 0.584 mmol) from Step 2 in tetrahydrofuran (6 mL) were added sodium borohydride (177 mg, 4.668 mmol) and tetrakis(triphenylphosphine)palladium (67.5 mg, 0.058 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and quenched with saturated ammonium chloride, extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. Flash chromatography on a Biotage® apparatus (silica gel, 10 to 50% tetrahydrofuran in hexanes gradient) gave the title compound (30, 459 mg, 0.58 mmol, 100%) as colorless oil.

Provenance & Evidence