HCID 15720054, compound → HCID 23238909, compound

HRID 277161Notes

Reaction equation

HRID 277161 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([CH3:19])[O:7][C@@H:6]1[N:20]=[N+]=[N-])(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([CH3:19])[O:7][C@@H:6]1[NH2:20])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 15720054HCID 15720054, compound

Product 1

HCID 23238909HCID 23238909, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,3,4-Tri-O-acetyl-beta-L-fucopyranosyl azide (Acros) (750 mg, 2.38 mmol) in 40 mL of EtOAc was added 120 mg of 10% Pd/C. This solution was stirred under an atmosphere of hydrogen gas (1 atm) for 3 hours. The mixture was filtered through a pad of Celite® and the pad was washed with EtOAc (25 mL). The solution was evaporated to afford the desired amine 148 (688 mg, 100%)

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washthe pad was washed with EtOAc (25 mL)
  3. customThe solution was evaporated

Sources & evidence

ORD record
ord-529bc3c3b90d437796807c2868427b0d
Source dataset
uspto-grants-2002_03
Patent number
US06355660B1

Reaction notes

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