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Water → 1-benzyloxycarbonyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazole

HRID 910594
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 910594
[CH2:1]([O:8][C:9]([N:11]1[C:15]([CH:16]([CH3:18])[CH3:17])=[C:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13](=[O:26])[NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:33]([O:39][C@@H:40]1[C@@H:45]([O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[C@H:44]([O:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[C@@H:43]([CH2:60][O:61][C:62](=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64])[O:42][C@@H:41]1Br)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35].O>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[C:15]([CH:16]([CH3:18])[CH3:17])=[C:14]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:13]([O:26][C@@H:41]2[O:42][C@H:43]([CH2:60][O:61][C:62](=[O:67])[C:63]([CH3:66])([CH3:65])[CH3:64])[C@@H:44]([O:53][C:54](=[O:59])[C:55]([CH3:56])([CH3:57])[CH3:58])[C@H:45]([O:46][C:47](=[O:52])[C:48]([CH3:49])([CH3:50])[CH3:51])[C@H:40]2[O:39][C:33](=[O:38])[C:34]([CH3:37])([CH3:35])[CH3:36])=[N:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10886360((2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl)methyl 2,2-dimethylpropanoateHCID 67350623HCID 67350623, Verbindung

Produkt 1

HCID 673498691-benzyloxycarbonyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyl-oxy)-1H-pyrazole
Ausbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyloxycarbonyl-4-benzyl-5-isopropyl-1,2-dihydro-3H-pyrazol-3-one (0.16 g) in acetonitrile (5 mL) were added potassium carbonate (0.0757 g) and 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (0.278 g) successively under stirring at room temperature. In addition, the mixture was stirred at 50° C. for 4 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/6) to give 1-benzyloxycarbonyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (0.228 g).

Aufarbeitung

  1. stirringIn addition, the mixture was stirred at 50° C. for 4 hours
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe insoluble materials were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/6)

Quellen und Nachweise

ORD-Eintrag
ord-eca43624fa67487faade8d1c0e792a10
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08022192B2

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