beta-D-Galactose pentaacetate → 4-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyloxy)-3-(2-phenylethyl)benzofuran

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To a solution of 4-hydroxy-3-(2-phenylethyl)benzofuran (0.11 g) and 1,2,3,4,6-penta-O-acetyl-β-D-galactopyranose (0.37 g) in dichloromethane (5 mL) was added boron trifluoride-diethyl ether complex (0.12 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1-3/2) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)-3-(2-phenylethyl)benzofuran (0.13 g). This material was dissolved in methanol (5 mL). To the solution was added sodium methoxide (28% methanol solution, 0.043 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (24 mg).

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