Reacción #43685

Ecuación de reacción

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

ethanethiol

potassium carbonate

→

title compound

Rendimiento 30.8%

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

Rendimiento 30.8%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with ethyl acetate
2. 2
   LavadoThe extract 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)-4-(2-phenylethyl)benzo[b]thiophene (0.58 g) and ethanethiol (1.13 mL) in dichloromethane (10 mL) was added boron trifluoride diethyl ether complex (1.43 mL) at room temperature, and the mixture was stirred for 3 hours. A saturated potassium carbonate aqueous solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (94 mg).

Fuente