反応 #6877

反応方程式

Nucleoside

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

→

nucleoside

収率 82.0%

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

収率 82.0%

溶媒

methanol

反応条件

後処理

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

実験手順

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.

出典