反応 #1474911

反応方程式

Compound 36

3′-O-benzyl-5′-O-t-butyldiphenylsilyl-4′-p-toluenesulfonyloxymethyl-5-methyluridine

sodium bis(trimethylsilyl)amide

sodium bicarbonate

→

Compound 37

収率 98.0%

3′-O-benzyl-5′-O-t-butyldiphenylsilyl-2′-O,4′-C-methylene-5-methyluridine

収率 98.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
2. 2
   workup.ADDITIONAfter water was added to the residue
3. 3
   抽出the mixture was extracted with chloroform
4. 4
   洗浄The organic phase was washed with a saturated sodium chloride solution
5. 5
   乾燥dried over sodium sulfate
6. 6
   workup.DISTILLATIONThe solvents were distilled off under reduced pressure
7. 7
   その他the resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 2:3)

実験手順

In a stream of nitrogen, sodium bis(trimethylsilyl)amide (1.0 M in THF, 8.47 ml, 8.47 mmols) was added, under cooling with ice, to a tetrahydrofuran solution (30 ml) of Compound 36 (1.86 g, 2.42 mmols), and the mixture was stirred for 1 hour at room temperature. A saturated sodium bicarbonate solution (14 ml) was added to the reaction mixture, and then the solvent was distilled off under reduced pressure. After water was added to the residue, the mixture was extracted with chloroform. The organic phase was washed with a saturated sodium chloride solution, and then dried over sodium sulfate. The solvents were distilled off under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 2:3) to obtain a white powder, Compound 37 (1.42 g, 2.37 mmols, 98%).

出典