Reacción #6121

Ecuación de reacción

4-nitrophenyl 1,5-dithio-β-D-xylopyranoside

→

expected product

Rendimiento 46.0%

4-aminophenyl 1,5-dithio-β-D-xylopyranoside

Rendimiento 46.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   Otrofor 3 days
3. 3
   workup.ADDITIONare added
4. 4
   OtroThe mixture obtained
5. 5
   Filtraciónis filtered
6. 6
   Otrothe solvent is evaporated off under reduced pressure
7. 7
   Otrothe residue obtained
8. 8
   Otrois purified by flash chromatography
9. 9
   Otrois then recrystallized from water

Procedimiento

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.

Fuente