反应详情

温度

60 °C

713 mg (2 mmol) of 3'-O-[(1,1-dimethylethyl)dimethylsilyl]thymidine [Can. J. Chem., 56, 2768 (1978)] were dissolved in 5 ml of tetrahydrofuran, and 175 mg (4 mmol) of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to the resulting solution under an argon atmosphere. The mixture was then stirred at 60° C. for 2 hours. At the end of this time, the temperature of the mixture was reduced to room temperature, and then 678 mg (2 mmol) of 3,4-dibenzyloxybenzyl chloride was added, followed by 149.9 mg (1 mmol) of sodium iodide, and the resulting mixture was stirred at room temperature for 19 hours, and then at 60° C. for 5 hours. At the end of this time, the solvent was distilled off under reduced pressure, and the residue was dissolved in 50 ml of ethyl acetate. The resulting solution was washed twice, each time with 50 ml of 0.01N aqueous hydrochloric acid; it was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 4 ml of tetrahydrofuran, and 4 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran was added to the solution. The mixture was then stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was dissolved in 50 ml of ethyl acetate. The resulting solution was washed twice, each time with 50 ml of a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was applied to a chromatography column [LiChroprep (trade mark) Si60, 40-63 μm, Groβe C, Merck] and eluted using a gradient elution method, with methylene chloride containing from 1 to 4% by volume of methanol, to give 345.4 mg (yield 31.7%) of the title compound.

1. customwas reduced to room temperature
2. stirringthe resulting mixture was stirred at room temperature for 19 hours
3. waitat 60° C. for 5 hours
4. distillationAt the end of this time, the solvent was distilled off under reduced pressure
5. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
6. washThe resulting solution was washed twice
7. dry with materialit was then dried over anhydrous magnesium sulfate
8. customThe solvent was removed by distillation under reduced pressure
9. dissolutionThe residue was dissolved in 4 ml of tetrahydrofuran
10. addition4 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran was added to the solution
11. stirringThe mixture was then stirred at room temperature for 2 hours
12. customAt the end of this time, the solvent was removed by distillation under reduced pressure
13. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
14. washThe resulting solution was washed twice
15. dry with materialeach time with 50 ml of a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
16. customThe solvent was then removed by distillation under reduced pressure
17. washeluted
18. washa gradient elution method