Reacción #43690

Ecuación de reacción

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

ethanethiol

potassium carbonate

→

title compound

Rendimiento 32.0%

2-(β-D-Glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene

Rendimiento 32.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was extracted with ethyl acetate
2. 2
   LavadoThe organic layer washed with 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: dichloromethane/methanol=10/1)

Procedimiento

To a solution of 2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene (0.95 g) and ethanethiol (1.8 mL) in dichloromethane (15 mL) was added boron trifluoride diethyl ether complex (2.1 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 hours, and a saturated potassium carbonate aqueous solution was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer washed with 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: dichloromethane/methanol=10/1) to give the title compound (0.16 g).

Fuente