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 49448Notes

Reaction equation

HRID 49448 reaction equation
[CH3:1][C:2]([O:4][CH2:5][C@H:6]1[O:11][C@H:10]([O:12][C:13]([CH3:15])=[O:14])[C@H:9]([N:16]=[N+]=[N-])[C@@H:8]([O:19][C:20]([CH3:22])=[O:21])[C@@H:7]1[O:23][C:24]([CH3:26])=[O:25])=[O:3]>CCOC(C)=O.[Pd]>[C:13]([O:12][C@H:10]1[O:11][C@H:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[C@@H:7]([O:23][C:24](=[O:25])[CH3:26])[C@H:8]([O:19][C:20](=[O:21])[CH3:22])[C@H:9]1[NH2:16])(=[O:14])[CH3:15]

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-21c48cd3a7d74f6fadbd7dcc8a5cfc32
Source dataset
uspto-grants-2004_03
Patent number
US06706740B2

Reaction notes

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