Methanol → HCID 11655639, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, dimethylsulfide (2.66 ml) and a boron trifluoride-diethyl ether complex (1.03 ml, 8.12 mmol) were added to a solution of (3R,4R,5S,6R)-3,4,5-trisbenzyloxy-2-benzyloxymethyl-6-[3-(5-ethylbenzo[b]-thiophen-2-ylmethyl)naphthalen-1-yl]tetrahydropyran (670 mg, 0.81 mmol) in methylene chloride (4 ml) under cooling with ice. The reaction mixture was stirred at room temperature for 1.5 days, and then a 50% methanol aqueous solution (20 ml) was added under cooling with ice and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried with sodium sulfate, and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (50:1)] to obtain the title compound (119 mg, 32%).

Provenance & Evidence