HCID 10970830, compound → HCID 86736895, compound

HRID 1660556Notes

Reaction equation

HRID 1660556 reaction equation
[N+]([O-])([O:3][C@H:4]1[O:17][C@H:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]([O:7][C:8](=[O:10])[CH3:9])[C@H:5]1[N:23]=[N+]=[N-])=O.[N+]([O-])(O[C@@H]1O[C@H](COC(=O)C)[C@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1N=[N+]=[N-])=O>C(O)(=O)C.[Pd]>[C:8]([O:7][C@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[O:17][CH:4]([OH:3])[C@@H:5]1[NH2:23])(=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 10970830HCID 10970830, compoundHCID 11728506α-D-Galactopyranose, 2-azido-2-deoxy-, 3,4,6-triacetate 1-nitrate

Product 1

HCID 86736895HCID 86736895, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of the anomeric mixture of the 2-azido-2-deoxy nitrates II and III (1.0 g, 7.68 mmole) was hydrogenated in acetic acid (5 ml) containing 5% palladium on carbon (0.10 g) at one atmosphere and ambient temperature for 5 hours. After removal of the catalyst by filtration and evaporation of the solvent gave 3,4,6-tri-O-acetyl-D-galactosamine (XXXVIII) (0.85 g) as a foam. Treatment of this foam with 2 aqueous hydrochloric acid (10 ml) at ambient temperature for two to three hours followed by dilution with n-butanol (5 ml) and evaporation gave D-galactosamine hydrochloride XXXVII (0.50 g) which was recrystallized from butanol-ethanol-water.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-d337d0654ca748d99ce4af99e76091e3
Source dataset
uspto-grants-1981_12
Patent number
US04308376

Reaction notes

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