Triphenylphosphine → HCID 71117288, compound

Participants

Reaction Steps

To a solution of ((2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-5-(4-ethoxybenzyl)-2-hydroxyphenyl)tetrahydro-2H-pyran-2-yl)methyl acetate (45, 2.19 g, 2.97 mmol) from Step 1 in tetrahydrofuran (30 mL) were added triphenylphosphine (1.57 g, 5.94 mmol) and cis-2-butene-1,4-diol (0.5 mL, 5.94 mmol) at 0° C., and diisopropyl azodicarboxylate (1.35 mL, 6.53 mmol) was added dropwise thereto. The reaction mixture was stirred at ambient temperature for 0.5 h and warmed up to room temperature for 4 h. After cooling to 0° C., the reaction mixture was quenched with H2O, extracted with ethyl acetate and dried over magnesium sulfate. The crude residue was purified on Biotage® purification apparatus (silica gel, 10 to 45% tetrahydrofuran in hexanes) to yield the title compound (46, 2.08 g, 2.57 mmol, 87%) as colorless oil.

Provenance & Evidence