Reaction #43685

Reaction equation

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

ethanethiol

potassium carbonate

→

title compound

Yield 30.8%

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

Yield 30.8%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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).

Source