反応 #965071

反応方程式

triethylamine trihydrofluoride

triethylamine

4,4′-dimethoxytrityl chloride

Compound 11

2′-O-(2-methoxyethyl)-5′-(R)-methyl-3′-O-tert-butyldimethylsilyl-5-methyluridine

→

Compound 12

収率 73.0%

5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-methoxyethyl)-5′(R)-methyl-5-methyluridine

収率 73.0%

溶媒

EtOAc

THF

反応条件

後処理

1. 1
   乾燥dried over P2O5 under reduced pressure
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in anhydrous pyridine (3 mL)
3. 3
   温度The reaction mixture was cooled to room temperature
4. 4
   workup.ADDITIONdiluted with EtOAc (40 mL)
5. 5
   洗浄washed with saturated aqueous NaHCO3 (60 mL) and brine (40 mL)
6. 6
   乾燥dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他The residue obtained
10. 10
    その他was purified by silica gel column chromatography
11. 11
    洗浄eluted first with 50% EtOAc in hexanes
12. 12
    その他The product obtained
13. 13
    洗浄washed with water (40 mL), saturated aqueous NaHCO3 (40 mL) and brine (40 mL)
14. 14
    乾燥then dried over Na2SO4
15. 15
    ろ過filtered
16. 16
    その他evaporated
17. 17
    その他The residue obtained
18. 18
    その他was purified by silica gel column chromatography
19. 19
    洗浄eluted with 70% EtOAc in hexanes

実験手順

Compound 11 (0.42 g, 0.96 mmol) was mixed with 4,4′-dimethoxytrityl chloride (0.82 g, 2.41 mmol) and dried over P2O5 under reduced pressure. The mixture was dissolved in anhydrous pyridine (3 mL) and stirred at 45° C. for 18 h under an atmosphere of argon. The reaction mixture was cooled to room temperature and diluted with EtOAc (40 mL) and washed with saturated aqueous NaHCO3 (60 mL) and brine (40 mL), dried over Na2SO4, filtered and concentrated. The residue obtained was purified by silica gel column chromatography and eluted first with 50% EtOAc in hexanes and then with 5% methanol in CH2Cl2. The product obtained was dissolved in a mixture of triethylamine trihydrofluoride (1.38 mL, 8.44 mmol) and triethylamine (0.58 mL, 4.22 mmol) in THF (8.4 mL). After 72 h the mixture was diluted with EtOAc (60 mL), washed with water (40 mL), saturated aqueous NaHCO3 (40 mL) and brine (40 mL) then dried over Na2SO4, filtered and evaporated. The residue obtained was purified by silica gel column chromatography and eluted with 70% EtOAc in hexanes to yield Compound 12 (0.44 g, 73%). ES MS m/z 631.2 [M+H]+.

出典