Reacción #6877

Ecuación de reacción

Nucleoside

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

→

nucleoside

Rendimiento 82.0%

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

Rendimiento 82.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was degassed
2. 2
   Filtraciónthe mixture was filtered (silica gel
3. 3
   Lavadowashed with dichloromethane/methanol (700 cm3
4. 4
   Concentración1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume
5. 5
   Filtraciónfiltration
6. 6
   Otrothe filtrate was evaporated to dryness under reduced pressure

Procedimiento

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.

Fuente