Boron trifluoride → HCID 56673701, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of crude (3R,4S,5S,6R)-6-(hydroxymethyl)-2-methoxy-2-(4-methyl-5-(4-propylbenzyl)thiophen-2-yl)tetrahydro-2H-pyran-3,4,5-triol (50) in DCM (11.8 mL) and ACN (11.8 mL) was added triethylsilane (0.786 mL, 4.90 mmol) followed by BF3 etherate (0.611 mL, 4.90 mmol) under nitrogen atmosphere at −60° C. The reaction temperature was maintained −60 to −30° C. for 2 hours. The reaction was quenched with a saturated NaHCO3 solution (20 mL), and then extracted with EtOAc (50 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by prep HPLC (C18) to provide the title compound 51 (391 mg, 0.996 mmol, 37%).

Provenance & Evidence