alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) → 4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-(2-phenylethyl)indole

Participants

Reaction Steps

To a solution of 4-hydroxy-3-(2-phenylethyl)indole (70 mg) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.22 g) in dichloromethane (3 mL) was added boron trifluoride-diethyl ether complex (0.081 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by preparative thin layer chromatography (eluent: n-hexane/ethyl acetate=1/1) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-phenylethyl)indole. This material was dissolved in tetrahydrofuran (1 mL)-methanol (0.5 mL). To the solution was added sodium methoxide (28% methanol solution, 0.024 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was purified by preparative thin layer chromatography (eluent: dichloromethane/methanol=5/1) to give the title compound (22 mg).

Provenance & Evidence