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 1278173Notes

Reaction equation

HRID 1278173 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].[H][H]>C(O)C.[Pt]=O>[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

5

Reactant 2

HCID 2725015beta-D-Glucopyranosyl azide, 2-(acetylamino)-2-deoxy-, 3,4,6-triacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 108933592-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosylamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Platinum oxide d (2.6 g) is added to a solution of 2.6 g of the azide in 150 ml of absolute ethanol, and the suspension is shaken with hydrogen gas for 1.5 hours at atmospheric pressure and room temperature. After the suspension is filtered three times on a celite column, the filtrate is evaporated to dryness. Recrystallization from CH2Cl2 -Et2O yields 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl amine.

Workup

  1. filtrationAfter the suspension is filtered three times on a celite column
  2. customthe filtrate is evaporated to dryness
  3. customRecrystallization from CH2Cl2 -Et2O

Sources & evidence

ORD record
ord-731f5956a2884110af910b0fbb99718d
Source dataset
uspto-grants-1981_07
Patent number
US04280953

Reaction notes

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