4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide → 4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galacto-pyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl amine

HRID 991156Notes

Reaction equation

HRID 991156 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]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[O:24][C@@H:25]1[C@@H:30]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[O:29][C@@H:28]([N:36]=[N+]=[N-])[C@H:27]([O:39][C:40](=[O:42])[CH3:41])[C@H:26]1[O:43][C:44](=[O:46])[CH3:45])(=[O:3])[CH3:2]>CO.[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]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[O:24][C@@H:25]1[C@@H:30]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[O:29][C@@H:28]([NH2:36])[C@H:27]([O:39][C:40](=[O:42])[CH3:41])[C@H:26]1[O:43][C:44](=[O:46])[CH3:45])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 233928434-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide

Product 1

HCID 233928414-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galacto-pyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl amineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide (178 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 4-O-(2,3,4,6-tetra-O-acetyl-α-D-galacto-pyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl amine (26) (157 mg, 92%).

Workup

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

Sources & evidence

ORD record
ord-f584a534e6044d5db6508d3180c3e4a9
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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