反应详情

温度

65 °C

To a pre-cooled (0° C.) solution of (2S,3R,4R,5R)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-2,3,4-triyl tribenzoate (or 2,3,4,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose) (CarboSynth Ltd, 10.0 g, 17.22 mmol), 2-amino-6-chloropurine (Aldrich, 3.2 g, 18.87 mmol), and 1,8-diazabicycl[5.4.0]undec-7-ene (DBU) (7.7 mL, 51 mmol) in anhydrous acetonitrile (200 mL), was added trimethysilyl triflate (12.5 mL, 68.8 mmol) dropwise. The reaction mixture was then heated at 65° C. for 4 to 6 h, allowed to cool down to room temperature, poured into saturated aqueous sodium bicarbonate (300 mL), and extracted with dichloromethane (3×150 mL). The combined organic phase was dried over sodium sulfate and evaporated under reduced pressure. The residue was precipitated from dichloromethane and methanol, filtrated, the solid was washed 2 times with methanol and dried to give the desired compound (8.5 g, 79%) as a white solid (yields are from 65% (column) up to 90% (precipitation)).

1. temperatureto cool down to room temperature
2. extractionextracted with dichloromethane (3×150 mL)
3. dry with materialThe combined organic phase was dried over sodium sulfate
4. customevaporated under reduced pressure
5. customThe residue was precipitated from dichloromethane and methanol
6. filtrationfiltrated
7. washthe solid was washed 2 times with methanol
8. customdried