Diiodomethane → HCID 86728591, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diiodomethane (0.66 mL, 8.09 mmol) in dichloromethane (10 mL) was added diethyl zinc (1.1M solution in toluene, 3.7 mL, 4.05 mmol) at 0° C. and stirred for 15 min. The reaction mixture was cooled to −78° C. and ((2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-5-(4-ethoxybenzyl)-2-((Z)-4-hydroxybut-2-enyloxy)phenyl)tetrahydro-2H-pyran-2-yl)methyl acetate (46, 0.82 mg, 1.01 mmol) in dichloromethane (5 mL) was added dropwise to the reaction mixture, slowly warmed up to −20° C. for 3 h. The reaction mixture was quenched with saturated ammonium chloride, extracted with ethyl acetate, and dried over magnesium sulfate. The organic layer was filtered and evaporated in vacuo and the residue was purified on a Biotage® apparatus (silica gel, 5 to 40% ethyl tetrahydrofuran in hexanes gradient) to give the title compound (47, 835 mg, 1.01 mmol, 100%, diastereomer in about 1:2 ratio) as colorless oil.

Provenance & Evidence