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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
ノート
印刷プレビュー

反応式

HRID 554564 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-1eaf7473534c44e092fd832a317b0749
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08048897B2

反応ノート

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