4-O-benzyl-3,6-di-O-acetyl-D-glucose → 3,6-di-O-acetyl-D-glucose

HRID 1422554Notes

Reaction equation

HRID 1422554 reaction equation
C([O:8][C@H:9]([C@@H:19]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[OH:20])[C@H:10]([O:15][C:16](=[O:18])[CH3:17])[C@@H:11]([OH:14])[CH:12]=[O:13])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:16]([O:15][C@@H:10]([C@@H:9]([C@@H:19]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[OH:20])[OH:8])[C@@H:11]([OH:14])[CH:12]=[O:13])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 866548394-O-benzyl-3,6-di-O-acetyl-D-glucoseHCID 178418361HCID 178418361, compound

Product 1

HCID 866548403,6-di-O-acetyl-D-glucose

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Degussa 10% Pd/C (50% wet) (0.4 g) was added to the solution of 4-O-benzyl-3,6-di-O-acetyl-D-glucose (5 mmol) in ethanol (50 mL). Obtained mixture was hydrogenated at room temperature using Paar apparatus with hydrogen (45 psi) After 12 hr reaction was completed (TLC), catalyst was filtered off and the solvent was evaporated to give a crude product. Product was purified by column chromatography (SilicaGel 60 Merck), using hexanes:ethyl acetate as eluent.

Workup

  1. customObtained mixture
  2. customwas hydrogenated at room temperature
  3. customAfter 12 hr
  4. customreaction
  5. filtrationwas filtered off
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a3b7de27c6b74290ae0a91850643d512
Source dataset
uspto-grants-2015_01
Patent number
US08927506B2

Reaction notes

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