HCID 68872621, compound → HCID 68873213, compound

HRID 1247735Notes

Reaction equation

HRID 1247735 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:36]([O:42][C:43](=[O:45])[CH3:44])[C@@H:35]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[O:34][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([NH:14]C(OCC2C=CC=CC=2)=O)[CH:11]=[CH:10][C:9]=1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=1)(=[O:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:36]([O:42][C:43](=[O:45])[CH3:44])[C@@H:35]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[O:34][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:9]=1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 68872621HCID 68872621, compound

Product 1

HCID 68873213HCID 68873213, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-benzyloxycarbonylamino-2-(4-ethyl-benzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.35 g) in tetrahydrofuran (4 mL) was added 10% palladium-carbon powder (0.07 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 8 hours. An insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/3-dichloromethane/ethyl acetate=1/1) to give 5-amino-2-(4-ethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.19 g).

Workup

  1. customAn insoluble material was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/3-dichloromethane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-7e9a490a58b845a99168ac0277e3634a
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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