Sodium Methoxide → Sergliflozin

Participants

Reaction Steps

Sodiummethoxide (28% methanol solution; 0. 12 mL) was added to a solution of 2-(4-methoxybenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.11 g) in methanol (4 mL), and the mixture was stirred at room temperature for 30 minutes. 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-methoxy-benzyl)phenyl β-D-glucopyranoside (65 mg). 1H-NMR (CD3OD) δ ppm: 3.35-3.55 (4H, m), 3.69 (1H, dd, J=5.1, 12.1 Hz), 3.73 (3H, s), 3.80-4.00 (2H, m), 4.03 (1H, d, J=15.1 Hz), 4.91 (1H, d, J=7.4 Hz), 6.75-6.85 (2H, m), 6.85-6.95 (1H, m), 6.95-7.10 (1H, m), 7.10-7.20 (4H, m)

Provenance & Evidence