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Dichloromethane → 4-(4-bromo-2-methylbenzyl)-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside

HRID 931671
ノート
印刷プレビュー

反応式

HRID 931671 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([OH:17])=[N:11][NH:12][C:13]=2[CH:14]([CH3:16])[CH3:15])=[C:4]([CH3:18])[CH:3]=1.[C:19]([OH:27])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:28]([OH:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:37]([OH:45])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[C:46]([OH:54])(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[C@H:55]1(Br)[O:63][C@H:62]([CH2:64]O)[C@@H:60](O)[C@H:58](O)[C@H:56]1O.ClCCl.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O>[C:19]([O:27][C@@H:56]1[C@@H:58]([O:35][C:28](=[O:36])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@H:60]([O:44][C:37](=[O:45])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:62]([CH2:64][O:53][C:46](=[O:54])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[O:63][C@H:55]1[O:17][C:10]1[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[CH3:18])=[C:13]([CH:14]([CH3:15])[CH3:16])[NH:12][N:11]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 86720879benzoic acid;(2R,3R,4S,5S,6R)-2-bromo-6-(hydroxymethyl)oxane-3,4,5-triolHCID 178422431HCID 178422431、化合物

生成物 1

HCID 867208784-(4-bromo-2-methylbenzyl)-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside収率 98.9%

試薬・触媒・溶媒 2

HCID 159952Benzyltributylammonium chloride触媒HCID 962Water溶媒

実験手順

To a 1 L flask, add 4-[(4-bromo-2-methyl-phenyl)methyl]-5-isopropyl-1H-pyrazol-3-ol (20 g, 64.7 mmol), alpha-D-glucopyranosyl bromide tetrabenzoate (50 g, 76 mmol), benzyltributylammonium chloride (6 g, 19.4 mmol), dichloromethane (500 mL), potassium carbonate (44.7 g, 323 mmol) and water (100 mL). Stir the reaction mixture overnight at room temperature. Extract with dichloromethane (500 mL). Wash extract with water (300 mL) and brine (500 mL). Dry organic phase over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography to yield the title compound (37 g, 64 mmol). MS (m/z): 889.2 (M+1), 887.2 (M−1).

後処理

  1. extractionExtract with dichloromethane (500 mL)
  2. washWash
  3. extractionextract with water (300 mL) and brine (500 mL)
  4. filtrationDry organic phase over sodium sulfate, filter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash chromatography

出典と根拠

ORDレコード
ord-e233bd226822492b8431f7a420d620e1
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296775B2

反応ノート

読み込み中…

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