4-nitrophenyl 1,5-dithio-beta-D-xylopyranoside → 4-aminophenyl 1,5-dithio-beta-D-xylopyranoside
Reaktionsgleichung
[S:1]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[C@@H:2]1[S:10][CH2:9][C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]>CO.[Pd]>[S:1]([C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)[C@@H:2]1[S:10][CH2:9][C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
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.