2-(Hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol → 4-Aminophenyl glucoside

HRID 460421Notes

Reaction equation

HRID 460421 reaction equation
[CH:1]1[C:6]([N+:7]([O-])=O)=[CH:5][CH:4]=[C:3]([O:10][CH:11]2[O:16][CH:15]([CH2:17][OH:18])[CH:14]([OH:19])[CH:13]([OH:20])[CH:12]2[OH:21])[CH:2]=1.[H][H]>CO.O1CCCC1.[C].[Pd]>[C@@H:11]1([O:10][C:3]2[CH:4]=[CH:5][C:6]([NH2:7])=[CH:1][CH:2]=2)[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([OH:19])[C@H:13]([OH:20])[C@H:12]1[OH:21]

Participants

5

Reactant 2

HCID 2593802-(Hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triolHCID 178418361HCID 178418361, compound

Product 1

HCID 887024-Aminophenyl glucosideYield 80%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

p-nitrophenyl-β-D-glucopyranoside (Tokyo Chemical Industries) (250 mg) was dissolved in a methanol/tetrahydrofuran mixed solvent (20 ml/5 ml), and 10% palladium carbon (250 mg) was added to this solution. Hydrogen gas was introduced under a nitrogen gas atmosphere into the reaction solution at room temperature for 3 hours. The reaction mixture was filtered to remove palladium carbon, the filtrate was evaporated under vacuum, and solidified. This residue was purified by silica gel chromatography using a tetrahydrofuran/chloroform mixed solvent (1/1, volume ratio) as an eluant, and p-aminophenol-β-D-glucopyranoside was obtained.

Workup

  1. additionwas added to this solution
  2. filtrationThe reaction mixture was filtered
  3. customto remove palladium carbon
  4. customthe filtrate was evaporated under vacuum
  5. customThis residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8ba473a36d854cb5bf97c4fdb34ec01f
Source dataset
uspto-grants-2007_03
Patent number
US07196178B2

Reaction notes

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