Dimethyl Sulfide → HCID 11626638、化合物
反応式
CSC.C([O:11][C@H:12]1[C@@H:17]([O:18]CC2C=CC=CC=2)[C@@H:16]([O:26]CC2C=CC=CC=2)[C@@H:15]([CH2:34][O:35]CC2C=CC=CC=2)[O:14][CH:13]1[C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[C:45]([CH2:53][C:54]2[S:58][C:57]3[CH:59]=[CH:60][C:61]([F:63])=[CH:62][C:56]=3[CH:55]=2)[CH:44]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:63][C:61]1[CH:60]=[CH:59][C:57]2[S:58][C:54]([CH2:53][C:45]3[CH:44]=[C:43]([C@H:13]4[C@H:12]([OH:11])[C@@H:17]([OH:18])[C@H:16]([OH:26])[C@@H:15]([CH2:34][OH:35])[O:14]4)[C:52]4[C:47]([CH:46]=3)=[CH:48][CH:49]=[CH:50][CH:51]=4)=[CH:55][C:56]=2[CH:62]=1参加物
5
実験手順
Under a nitrogen atmosphere, dimethylsulfide (1.72 ml) and a boron trifluoride-diethyl ether complex (0.86 ml, 6.8 mmol) were added to a solution of (3R,4R,5S,6R)-3,4,5-trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-fluorobenzo[b]-thiophen-2-ylmethyl)naphthalen-1-yl]tetrahydropyran (550 mg, 0.68 mmol) in methylene chloride (15 ml) under cooling with ice. The reaction mixture was stirred at room temperature for 2.5 days, 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 then dried with sodium sulfate, and thereafter the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (40:1)] to obtain the title compound (140 mg, 46%).