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

HRID 910595Notes

Reaction equation

HRID 910595 reaction equation
C(OC([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][C@@H:27]2[O:53][C@H:52]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[C@@H:44]([O:45][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48])[C@H:36]([O:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[C@H:28]2[O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[N:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[CH2:19]([C:14]1[C:13]([O:26][C@@H:27]2[O:53][C@H:52]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:58])([CH3:60])[CH3:59])[C@@H:44]([O:45][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48])[C@H:36]([O:37][C:38](=[O:43])[C:39]([CH3:40])([CH3:42])[CH3:41])[C@H:28]2[O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:32])[CH3:33])=[N:12][NH:11][C:15]=1[CH:16]([CH3:18])[CH3:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

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

Product 1

HCID 673494844-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-betaD-glucopyranosyloxy)-1H-pyrazoleYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzyloxycarbonyl-4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (0.228 g) in methanol (5 mL) was added 10% palladium on carbon (50% wet: 0.40 g). In addition, the mixture was stirred under a hydrogen atmosphere at room temperature for 13 hours. The insoluble materials were removed by filtration through Celite®, and the filtrate was concentrated under reduced pressure to give 4-benzyl-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.186 g).

Workup

  1. customThe insoluble materials were removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-571a1aa8c1294caa9fd48639201e84b9
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

Loading…