Reaktion #6877

Reaktionsgleichung

Nucleoside

(1R,3R,4R,7R)-7-Benzyloxy-1-(4,4′-dimethoxytrityloxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

→

nucleoside

Ausbeute 82.0%

(1S,3R,4R,7R)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo [2.2.1]heptane

Ausbeute 82.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   Filtrationthe mixture was filtered (silica gel
3. 3
   Waschenwashed with dichloromethane/methanol (700 cm3
4. 4
   Einengen1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume
5. 5
   Filtrationfiltration
6. 6
   Sonstigethe filtrate was evaporated to dryness under reduced pressure

Vorschrift

Nucleoside 8 (3.09 g, 4.66 mmol) was dissolved in methanol (40 cm3) and 10% palladium on carbon (3 g, suspended in methanol (20 cm3)) was added. The mixture was degassed and stirred under an atmosphere of hydrogen. After 26 h, the mixture was filtered (silica gel, washed with dichloromethane/methanol (700 cm3; 1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume. After repeated filtration, the filtrate was evaporated to dryness under reduced pressure and the residue was subjected to column chromatography on silica gel using dichloromethane/methanol (5–12% methanol, v/v) as eluent furnishing nucleoside 9 (1.03 g, 82%) as a white solid material after evaporation of the solvents under reduced pressure.

Quelle