HCID 69135288, Verbindung → 4-{[4-(4-hydroxy-phenyl)phenyl]methyl}-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 7378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 7378
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]3[C:23]([O:28][C@@H:29]4[O:46][C@H:45]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[C@@H:40]([O:41][C:42](=[O:44])[CH3:43])[C@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]4[O:31][C:32](=[O:34])[CH3:33])=[N:24][NH:25][C:26]=3[CH3:27])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]3[C:23]([O:28][C@@H:29]4[O:46][C@H:45]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[C@@H:40]([O:41][C:42](=[O:44])[CH3:43])[C@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]4[O:31][C:32](=[O:34])[CH3:33])=[N:24][NH:25][C:26]=3[CH3:27])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Komponenten

4

Edukt 1

HCID 69135288HCID 69135288, Verbindung

Produkt 1

HCID 691338874-{[4-(4-hydroxy-phenyl)phenyl]methyl}-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazoleAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-({4-[4-(benzyloxy)phenyl]phenyl}methyl)-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.14 g) in methanol (3 mL) was added 10% palladium-carbon powder (0.030 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 11 hours. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=1/1-1/5-dichloromethane/methanol=10/1) to give 4-{[4-(4-hydroxyphenyl)phenyl]methyl}-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.071 g).

Aufarbeitung

  1. customInsoluble materials were removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customThe residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=1/1-1/5-dichloromethane/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-e4b9bbe846834bb582b1056ba6ea5d4b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087579B2

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