반응 #6877

반응 방정식

Nucleoside

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

→

nucleoside

수율 82.0%

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

수율 82.0%

용매

methanol

반응 조건

후처리

1. 1
   기타The mixture was degassed
2. 2
   여과the mixture was filtered (silica gel
3. 3
   세척washed with dichloromethane/methanol (700 cm3
4. 4
   농축1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume
5. 5
   여과filtration
6. 6
   기타the filtrate was evaporated to dryness under reduced pressure

실험 절차

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.

출처