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

HRID 1445336

Reaktionsgleichung

Reaktionsgleichung von HRID 1445336
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159952Benzyltributylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-dc2315c6fe0a424bafa9c03aefab94e1
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666848B2

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