Methanol → HCID 11610417、化合物

反応式

B(Cl)(Cl)Cl.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][C@H:21]2[C@H:26]([O:27]CC3C=CC=CC=3)[C@@H:25]([O:35]CC3C=CC=CC=3)[C@H:24]([O:43]CC3C=CC=CC=3)[C:23]([CH2:51][O:52]CC3C=CC=CC=3)=[CH:22]2)=[CH:9][CH:8]=1.CO>C(Cl)Cl>[OH:52][CH2:51][C:23]1[C@@H:24]([OH:43])[C@H:25]([OH:35])[C@@H:26]([OH:27])[C@H:21]([O:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:12][CH:11]=2)[CH:22]=1

参加物

実験手順

In a nitrogen stream, a boron trichloride 1.0 M methylene chloride solution (6.0 mL, 6.0 mmol) was added to a solution of 1-(4-methoxyphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)cyclohex-2-enyloxy]benzene (312 mg, 0.426 mmol) in methylene chloride (12 mL) at −78° C., and the mixture was stirred at the temperature for 1.5 hours. After addition of methanol, the temperature of the resulting solution was raised to room temperature and the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methanol:methylene chloride (1:8)] to obtain the title compound (37.9 mg, 24%).