Réaction #6121

ord-27586a11f84249d2aead91f87b678a79

Équation de réaction

O=[N+]([O-])c1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1
4-nitrophenyl 1,5-dithio-β-D-xylopyranoside
→
Nc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1
expected product
Rendement 46.0%
Nc1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1
4-aminophenyl 1,5-dithio-β-D-xylopyranoside
Rendement 46.0%

Réactifs

O=[N+]([O-])c1ccc(S[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)cc1
4-nitrophenyl 1,5-dithio-β-D-xylopyranoside

Réactifs

[Pd]
palladium-on-charcoal
[Pd]
palladium-on-charcoal

Solvants

CO
methanol

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreat room temperature
  2. 2
    Autrefor 3 days
  3. 3
    workup.ADDITIONare added
  4. 4
    AutreThe mixture obtained
  5. 5
    Filtrationis filtered
  6. 6
    Autrethe solvent is evaporated off under reduced pressure
  7. 7
    Autrethe residue obtained
  8. 8
    Autreis purified by flash chromatography
  9. 9
    Autreis then recrystallized from water

Mode opératoire

170 mg of 10% palladium-on-charcoal are added to a solution of 1.7 g (5.61.10-3 mol) of 4-nitrophenyl 1,5-dithio-β-D-xylopyranoside in 150 ml of methanol. The reaction medium is kept under hydrogen pressure (3.5.105Pa) at room temperature for 3 days. Repeat amounts of 170 mg of 10% palladium-on-charcoal are added after stirring for 3 hours, 4 hours, 12 hours and 24 hours. The mixture obtained is filtered, the solvent is evaporated off under reduced pressure and the residue obtained is purified by flash chromatography using a CHCl3 /CH3OH mixture (9/1 v/v) as the eluent, and is then recrystallized from water to give 0.7 g (yield: 46%) of the expected product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05246961uspto-grants-1993_09