Reacción #1447107

Ecuación de reacción

ethyl acetate

water

3-(4-ethylbenzyl)-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene

hydrogen peroxide

→

3-(4-Ethylbenzyl)-1-hydroxy-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic layer is separated
2. 2
   Lavadowashed with aqueous NaHCO3 solution, water and brine
3. 3
   SecadoAfter drying (magnesium sulphate) of the organic solution
4. 4
   Otrothe solvent is removed under reduced pressure
5. 5
   Otrothe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 2:1->1:2)

Procedimiento

A solution of 3-(4-ethylbenzyl)-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (0.64 g) in acetic acid (3 mL) is treated with hydrogen peroxide solution (0.2 mL, 35% in water) for 3 h. Then, ethyl acetate and water are added. The organic layer is separated and washed with aqueous NaHCO3 solution, water and brine. After drying (magnesium sulphate) of the organic solution, the solvent is removed under reduced pressure and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 2:1->1:2).

Fuente