Reacción #1528404

ord-553b220e24eb4344a28a52a77e5c1941

Ecuación de reacción

CC(=O)OC[C@H]1O[C@@H](Oc2nc(C)cc(C)c2Cc2ccc(C)c(F)c2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
2-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-3-(3-fluoro-4-methylbenzyl)-4,6-dimethyl-pyridine
C[O-].[Na+]
sodium methoxide
Cc1cc(C)c(Cc2ccc(C)c(F)c2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)n1
title compound
Rendimiento 67.3%
Cc1cc(C)c(Cc2ccc(C)c(F)c2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)n1
2-(β-D-Glucopyranosyloxy)-3-(3-fluoro-4-methylbenzyl)-4,6-dimethylpyridine
Rendimiento 67.3%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07655633B2uspto-grants-2010_02