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

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Reaction Steps

In a nitrogen stream, triethylsilane (0.34 ml, 2.06 mmol) and a boron trifluoride-diethyl ether complex (0.24 ml, 1.89 mmol) were added dropwise to a solution of (3R,4S,5S,6R)-2-[3-(benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-ol (1.4 g, 1.72 mmol) in methylene chloride (15 ml) at 0° C. The reaction mixture was stirred at room temperature for two hours, and then water was added thereto and extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate n-hexane (1:10)] to obtain the title compound (1.1 g, 80.2%).

Provenance & Evidence