Reacción #6883

Ecuación de reacción

Nucleoside

(1S,4R,5R,7R,8R)-4,8-Dibenzyloxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane

→

nucleoside

(1S,4R,5R,7R,8R)-4,8-Dihydroxy-7-(thymin-1-yl)-2,6-dioxabicyclo[3.2.1]octane

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was degassed
2. 2
   Filtraciónwas filtered off
3. 3
   Lavado(silica gel, washed with methanol, 400 cm3)
4. 4
   Concentraciónthe filtrate was concentrated to dryness under reduced pressure

Procedimiento

Nucleoside 18 (0.27 g, 0.60 mmol) was dissolved in absolute ethanol (20 cm3) and 20% palladium hydroxide on carbon (0.25 g) was added. The mixture was degassed and placed under an atmosphere of hydrogen. After stirring for 26 h the catalyst was filtered off (silica gel, washed with methanol, 400 cm3) and the filtrate was concentrated to dryness under reduced pressure. The residue was subjected to column chromatography on silica gel using dichloromethane/methanol (94:6, v/v) as eluent to give nucleoside 19 as white solid material (0.16 g, 98%) after evaporation of the solvents under reduced pressure.

Fuente