beta-D-Glucopyranosyl azide, 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate → 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosylamine

HRID 991150Notes

Reaction equation

HRID 991150 reaction equation
[C:1]([NH: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]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[N:24]=[N+]=[N-])(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([NH: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]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[NH2:24])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 2725015beta-D-Glucopyranosyl azide, 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate

Product 1

HCID 108933592-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosylamineYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl azide (100 mg, 0.26 mmol) was dissolved in MeOH (5 ml) and hydrogenated over Pd/C (10%) (10 mg) for 5 h. The suspension was filtered, and the filtrate was evaporated to give 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl amine (18) (80 mg, 86%).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-0135baa0b03748e2a27317789dde5fc1
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

Loading…