Dimethyl Sulfide → HCID 59869307, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, dimethylsulfide (0.66 ml) and a boron trifluoride-diethyl ether complex (0.33 ml, 2.62 mmol) were added to a solution of (2R,3S,4R,5R)-3,4,5-trisbenzyloxy-2-benzyloxymethyl-6-[3-(5-methoxybenzo-[b]thiophen-2-ylmethyl)-naphthalen-1-yl]tetrahydropyran (217 ml, 0.262 mmol) in methylene chloride (4 ml) under cooling with ice. The reaction mixture was stirred at room temperature for three days, and then a saturated sodium hydrogen carbonate aqueous solution 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 and the obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (30:1)] to obtain the title compound (85 mg, 65%).

Provenance & Evidence