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

Participants

Reaction Steps

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%).

Provenance & Evidence