تفاعل #1447107

معادلة التفاعل

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

المذيبات

acetic acid

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر