Reaction #1528404

Reaction equation

2-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-3-(3-fluoro-4-methylbenzyl)-4,6-dimethyl-pyridine

sodium methoxide

→

title compound

Yield 67.3%

2-(β-D-Glucopyranosyloxy)-3-(3-fluoro-4-methylbenzyl)-4,6-dimethylpyridine

Yield 67.3%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe solvent of the reaction mixture was removed
2. 2
   Otherthe residue was purified by column chromatography on silica gel (dichloromethane/methanol=10/1)

Procedure

To a solution of 2-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-3-(3-fluoro-4-methylbenzyl)-4,6-dimethyl-pyridine (0.17 g) in methanol (5 mL) was added sodium methoxide (28% methanol solution, 0.028 mL), and the mixture was stirred at room temperature for 1 hour. The solvent of the reaction mixture was removed, and the residue was purified by column chromatography on silica gel (dichloromethane/methanol=10/1) to give the title compound (0.081 g).

Source