反应 #6877

反应方程式

Nucleoside

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

→

nucleoside

收率 82.0%

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

收率 82.0%

溶剂

methanol

反应条件

后处理

1. 1
   其他The mixture was degassed
2. 2
   过滤the mixture was filtered (silica gel
3. 3
   洗涤washed with dichloromethane/methanol (700 cm3
4. 4
   浓缩1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume
5. 5
   过滤filtration
6. 6
   其他the filtrate was evaporated to dryness under reduced pressure

实验过程

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.

来源