反応 #965070

反応方程式

Compound 10

5′-O-Benzoyl-2′-O-(2-methoxyethyl)-5′-(R)-methyl-5-methyluridine

imidazole

tert-butyldimethylsilyl chloride

→

Compound 11

収率 89.0%

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

収率 89.0%

溶媒

DMF

ammonia

EtOAc

反応条件

後処理

1. 1
   洗浄washed with saturated aqueous NaHCO3 (2×60 mL) and brine (50 mL)
2. 2
   乾燥dried over Na2SO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他The residue obtained
6. 6
   workup.STIRRINGstirred for 24 h at 55° C
7. 7
   その他The solvent was removed under reduced pressure
8. 8
   その他the residue was purified by silica gel column chromatography
9. 9
   洗浄eluted with 50% EtOAc in hexanes

実験手順

A mixture of Compound 10 (1.33 g, 3.06 mmol) and imidazole (2.09, 30.70 mmol) was dissolved in anhydrous DMF (11.4 mL). To this solution tert-butyldimethylsilyl chloride (2.31 g, 15.33 mmol) was added with stirring at room temperature for 16 h under an atmosphere of argon. The reaction mixture was diluted with EtOAc (75 mL) and washed with saturated aqueous NaHCO3 (2×60 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated. The residue obtained was dissolved in methanolic ammonia (20 mL, 7 M) and stirred for 24 h at 55° C. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography and eluted with 50% EtOAc in hexanes to yield Compound 11 (1.21 g, 89%). ES MS m/z 455.2 [M+H]+.

出典