Water → (2S,3R,4R,5S,6R)-2-[3-(Benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-6-hydroxymethyltetrahydro-pyran-3,4,5-triol

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Reaction Steps

In a nitrogen stream, dimethylsulfide (3.5 ml) and boron trifluoride-diethyl ether complex (1.75 ml, 13.8 mmol) were added dropwise to an solution of (2S,3R,4R,5S,6R)-2-[3-(benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran (1.1 g, 1.38 mmol) in anhydrous methylene chloride (30 ml) at 0° C. and the reaction mixture was stirred at room temperature for three days. Water (10 ml) was added thereto and the resulting mixture was then extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate. After filtration, the solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel flash column chromatography [methylene chloride:methanol (30:1)] to obtain the title compound (0.35 g, 58.2%).

Provenance & Evidence