Reacción #43689

Ecuación de reacción

2,3,4,6-tetra-O-benzyl-1-[7-(4-methylbenzyl)benzo[b]thiophen-2-yl]-D-glucopyranose

triethylsilane

potassium carbonate

→

title compound

Rendimiento 80.8%

2-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene

Rendimiento 80.8%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with diethyl ether
2. 2
   LavadoThe organic layer washed with water and brine
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   OtroThe solvent was removed under reduced pressure
5. 5
   Otrothe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1)

Procedimiento

To a solution of 2,3,4,6-tetra-O-benzyl-1-[7-(4-methylbenzyl)benzo[b]thiophen-2-yl]-D-glucopyranose (1.2 g) and triethylsilane (0.49 mL), in acetonitrile (15 μL) was added boron trifluoride diethyl ether complex (2.0 mL) at −20° C., and the mixture was stirred for 1 hour. A saturated potassium carbonate aqueous solution was added to the mixture, and the mixture was extracted with diethyl ether. The organic layer washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1) to give the title compound (0.95 g).

Fuente