4-(2-Benzyloxybenzyl)-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole → 3-(beta-D-glucopyranosyloxy)-4-(2-hydroxybenzyl)-5-isopropyl-1H-pyrazole

HRID 1351101Notes

Reaction equation

HRID 1351101 reaction equation
C([O:8][C:9]1[CH:35]=[CH:34][CH:33]=[CH:32][C:10]=1[CH2:11][C:12]1[C:13]([O:20][C@@H:21]2[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]2[OH:23])=[N:14][NH:15][C:16]=1[CH:17]([CH3:19])[CH3:18])C1C=CC=CC=1>CO.[C].[Pd]>[C@@H:21]1([O:20][C:13]2[C:12]([CH2:11][C:10]3[CH:32]=[CH:33][CH:34]=[CH:35][C:9]=3[OH:8])=[C:16]([CH:17]([CH3:19])[CH3:18])[NH:15][N:14]=2)[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]1[OH:23]

Participants

4

Reactant 1

HCID 99569754-(2-Benzyloxybenzyl)-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

Product 1

HCID 695165493-(beta-D-glucopyranosyloxy)-4-(2-hydroxybenzyl)-5-isopropyl-1H-pyrazoleYield 89.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(2-benzyloxybenzyl)-3-(β-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole (200 mg) in methanol (5 mL) was added 10% palladium-carbon powder (40 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The insoluble material was removed by filtration, and the firtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=6/1) to give the title compound (146 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe firtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=6/1)

Sources & evidence

ORD record
ord-df781e145b4749d5bc3de90ad0f7c070
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

Loading…