Water → (4,5-Diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzoyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) acetate

HRID 1445336

反応式

HRID 1445336 の反応式
[OH:1][C:2]1[CH:6]=[C:5]([CH:7]([CH3:9])[CH3:8])[S:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11].[C:20]([O:23][CH:24]1[CH:29]([O:30][C:31](=[O:33])[CH3:32])[CH:28]([O:34][C:35](=[O:37])[CH3:36])[CH:27]([CH2:38][O:39][C:40](=[O:42])[CH3:41])[O:26][CH:25]1Br)(=[O:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[C:20]([O:23][CH:24]1[CH:29]([O:30][C:31](=[O:33])[CH3:32])[CH:28]([O:34][C:35](=[O:37])[CH3:36])[CH:27]([CH2:38][O:39][C:40](=[O:42])[CH3:41])[O:26][CH:25]1[O:1][C:2]1[CH:6]=[C:5]([CH:7]([CH3:9])[CH3:8])[S:4][C:3]=1[C:10](=[O:11])[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)(=[O:22])[CH3:21]

参加物

7

反応物 4

HCID 962Water2 回HCID 11430Potassium CarbonateHCID 102932alpha-D-Galactopyranosyl bromide, tetraacetateHCID 135744176647833-95-2

生成物 1

HCID 21045301(4,5-Diacetoxy-6-acetoxymethyl-2-[5-isopropyl-2-(4-methoxy-benzoyl)-thiophen-3-yloxy]-tetrahydro-pyran-3-yl) acetate

試薬・触媒・溶媒 2

HCID 159952Benzyltributylammonium chloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
22 °C

実験手順

380 mg of (3-hydroxy-5-isopropyl-thiophen-2-yl)-(4-methoxy-phenyl)-methanone, 848 mg of 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl acetate, 1.43 g of potassium carbonate and 71.1 mg of benzyltributylammonium chloride were dissolved in 20 ml of dichloromethane, and 1.20 ml of water were added. The reaction mixture was stirred at 22° C. for 40 h. 50 ml of water were added to the reaction mixture, which was extracted twice with 50 ml of dichloromethane each time. The combined organic phases were washed with 50 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:1).

後処理

  1. extractionwas extracted twice with 50 ml of dichloromethane each time
  2. washThe combined organic phases were washed with 50 ml of saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:1)

出典と根拠

ORDレコード
ord-dc2315c6fe0a424bafa9c03aefab94e1
出典データセット
uspto-grants-2010_02
特許番号
US07666848B2

関連ノート

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