1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranose → [(2R,3S,4R,5R,6R)-3,4,6-triacetyloxy-5-aminooxan-2-yl]methyl acetate

HRID 277162Notes

Reaction equation

HRID 277162 reaction equation
[C:1]([O:4][C@H:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[N:24]=[N+]=[N-])(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:4][C@H:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[NH2:24])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 121160661,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranose

Product 1

HCID 11121562[(2R,3S,4R,5R,6R)-3,4,6-triacetyloxy-5-aminooxan-2-yl]methyl acetateYield 101.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranose (TCI-US) (300 mg, 0.80 mmol) in 25 mL of EtOAc was added 180 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 (20 mL). The solution was evaporated to afford the desired amine 149 (282 mg, 100%).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washthe pad was washed with EtOAc (20 mL)
  3. customThe solution was evaporated

Sources & evidence

ORD record
ord-da75e182a7af46c898dd0bb2caf3775c
Source dataset
uspto-grants-2002_03
Patent number
US06355660B1

Reaction notes

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