Sodium Bicarbonate → HCID 68872067, compound

Participants

Reaction Steps

To a solution of 2-[4-(2-benzyloxyethyl)benzyl]phenol (3.2 g) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (12 g) in toluene (34 mL) and dichloromethane (17 mL) was added boron trifluoride diethyl ether complex (3.8 mL), and the mixture was stirred at room temperature for 14 hours. To the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (50 mL), and to the solution was added sodium methoxide (28% methanol solution, 0.39 mL). The resulting mixture was stirred at room temperature for 2.5 hours. The solvent of the reaction mixture was removed under reduced pressure, and to the residue was added water. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 2-[4-(2-benzyloxyethyl)benzyl]phenyl β-D-glucopyranoside (3.4 g).

Provenance & Evidence