반응 #1447107

반응 방정식

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

용매

acetic acid

반응 조건

후처리

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

실험 절차

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).

출처