Reaktion #43685

Reaktionsgleichung

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

ethanethiol

potassium carbonate

→

title compound

Ausbeute 30.8%

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

Ausbeute 30.8%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate
2. 2
   WaschenThe extract washed with brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Sonstigethe solvent was removed under reduced pressure
5. 5
   SonstigeThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Vorschrift

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).

Quelle