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Methanol → (1R,2S,3R,6R)-6-[2-(4-Cyclopropyl-benzyl)phenoxy]-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol

HRID 554564
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HRID 554564 반응식
B(Cl)(Cl)Cl.[CH:5]1([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C@H:22]3[C@H:27]([O:28]CC4C=CC=CC=4)[C@@H:26]([O:36]CC4C=CC=CC=4)[C@H:25]([O:44]CC4C=CC=CC=4)[C:24]([CH2:52][O:53]CC4C=CC=CC=4)=[CH:23]3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1.CC1C(C)=C(C)C(C)=C(C)C=1.CO>C(Cl)Cl>[CH:5]1([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C@H:22]3[C@H:27]([OH:28])[C@@H:26]([OH:36])[C@H:25]([OH:44])[C:24]([CH2:52][OH:53])=[CH:23]3)=[CH:12][CH:13]=2)[CH2:7][CH2:6]1
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6

반응물 4

HCID 887MethanolHCID 12784PentamethylbenzeneHCID 25135Boron TrichlorideHCID 674611171-(4-Cyclopropylphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyloxy]benzene

생성물 1

HCID 11625132(1R,2S,3R,6R)-6-[2-(4-Cyclopropyl-benzyl)phenoxy]-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a nitrogen stream, a boron trichloride 1.0 M methylene chloride solution (160 μL, 0.16 mmol) was added to a solution of 1-(4-cyclopropylphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyloxy]benzene (12 mg, 0.016 mmol) and pentamethylbenzene (24 mg, 0.17 mmol) in methylene chloride (300 μL) at −78° C., and the mixture was stirred at the same 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 preparative TLC [developing solution=methanol:methylene chloride (1:8)] to obtain the title compound (4.1 mg, 70%).

후처리

  1. distillationthe solvent was distilled under reduced pressure
  2. customThe obtained residue was purified by preparative TLC [developing solution=methanol:methylene chloride (1:8)]

출처 및 근거

ORD 기록
ord-1eaf7473534c44e092fd832a317b0749
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08048897B2

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