Reacción #1447108

Ecuación de reacción

Diethyl azodicarboxylate

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

cyclobutanol

triphenylphosphine

→

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

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is heated
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   Otrothe solvent is evaporated
4. 4
   Otrothe residue is purified by chromatography (cyclohexane/ethyl acetate 4:1->1:3) on silica gel

Procedimiento

Diethyl azodicarboxylate (0.38 g) dissolved in THF (0.5 mL) is added to 3-(4-ethylbenzyl)-1-hydroxy-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (0.27 g), cyclobutanol (0.1 mL) and triphenylphosphine (0.56 g) dissolved in THF (2 mL). The mixture is heated with stirring at 70° C. overnight. After cooling to room temperature, the solvent is evaporated and the residue is purified by chromatography (cyclohexane/ethyl acetate 4:1->1:3) on silica gel.

Fuente