反応 #331441

反応方程式

Potassium carbonate

water

methyl alcohol

Compound 35

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

→

Compound 36

収率 92.0%

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

収率 92.0%

溶媒

acetic acid

反応条件

後処理

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   workup.DISTILLATIONwhereafter the solvent was distilled off under reduced pressure
3. 3
   workup.ADDITIONAfter water was added to the residue
4. 4
   抽出the mixture was extracted with ethyl acetate
5. 5
   洗浄The organic phase was washed with a saturated sodium chloride solution
6. 6
   乾燥dried over sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   その他the resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 3:2)

実験手順

Potassium carbonate (12.75 mg, 0.0923 mmol) and water (0.5 ml) were added, under cooling with ice, to a methyl alcohol solution (4 ml) of Compound 35 (250 mg, 0.308 mmol), and the mixture was stirred for 22 hours at room temperature. Under cooling with ice, acetic acid was added to the reaction mixture to neutralize it, whereafter the solvent was distilled off under reduced pressure. After water was added to the residue, the mixture was extracted with ethyl acetate. The organic phase was washed with a saturated sodium chloride solution, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and then the resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 3:2) to obtain a white powder, Compound 36 (216.7 mg, 0.283 mmol, 92%). mp. 74-77° C. [α]D23 +5.15° (c=1.23, CHCl3). IR ν max (KBr): 3048, 2934, 1695, 1363, 1181, 1108, 977, 819, 704 cm−1.

出典