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

HRID 457505Notes

Reaction equation

HRID 457505 reaction equation
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

Participants

4

Reactant 1

HCID 69135288HCID 69135288, compound

Product 1

HCID 691338874-{[4-(4-hydroxy-phenyl)phenyl]methyl}-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazoleYield 58.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-3dff8ea5a0a94832ba08f8cebfbfa0b2
Source dataset
uspto-grants-2007_03
Patent number
US07189702B2

Reaction notes

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