Boron trifluoride etherate → (3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)-5-methoxyphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Participants

Reaction Conditions

Reaction Steps

To a solution of triol 74-3 (6.6 g, 14.14 mmol) in CH2Cl2/CH3CN (70 mL/70 mL) were added triethylsilane (4.5 mL, 28.28 mmol) and boron trifluoride diethyl etherate (3.6 mL, 28.28 mmol) at −50° C. The mixture was warmed up to 0° C. slowly and stirred at 0° C. for 2 hours. To the mixture was added aq. saturated NaHCO3 solution (50 mL) slowly and extracted with EtOAc (100 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was carried on to the next step without purification.

Provenance & Evidence