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

HRID 1445336

반응식

HRID 1445336 반응식
[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]

참가 물질

7

반응물 4

HCID 962Water2회HCID 11430Potassium CarbonateHCID 102932alpha-D-Galactopyranosyl bromide, tetraacetateHCID 135744176647833-95-2

생성물 1

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

시약·촉매·용매 2

HCID 159952Benzyltributylammonium chloride촉매HCID 6344Dichloromethane용매

반응 조건

온도
22 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dc2315c6fe0a424bafa9c03aefab94e1
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666848B2

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