反応 #978404

反応方程式

succinic anhydride

4,4′-Dimethoxytrityl chloride

2′-O-(2-methoxyethyl)-5-methyluridine

methanol

→

solid

収率 90.0%

Triethylammonium 5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-methoxyethyl)-5-methyluridine-3′-O-succinate

収率 90.0%

溶媒

triethylamine

acetonitrile

2,6-lutidine

反応条件

後処理

1. 1
   workup.WAITAfter 10 min.
2. 2
   workup.STIRRINGthe mixture was stirred overnight
3. 3
   濃縮The mixture was concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (200 ml)
5. 5
   洗浄washed with triethylammonium phosphate (0.5 M, pH 7, 3×100 ml)
6. 6
   乾燥The organic layer was dried (Na2SO4)
7. 7
   その他evaporated to approximately 100 ml
8. 8
   workup.ADDITIONHexane (150 ml) was added
9. 9
   workup.STIRRINGThe mixture was shaken for 5 min.
10. 10
    その他the supernatant was decanted
11. 11
    その他The residue was dried

実験手順

2′-O-(2-methoxyethyl)-5-methyluridine (MOE T, 15.8 g, 50 mmol) was dissolved in 2,6-lutidine (23.3 ml) and acetonitrile (150 ml). 4,4′-Dimethoxytrityl chloride (DMTCl, 18.6 g, 55 mmol) was added. The mixture was stirred at room temperature for 30 min. and methanol (MeOH, 0.2 ml) was added. After 10 min., triethylamine (20 ml) and succinic anhydride (15 g) were added and the mixture was stirred overnight. The mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane (200 ml) and washed with triethylammonium phosphate (0.5 M, pH 7, 3×100 ml). The organic layer was dried (Na2SO4) and evaporated to approximately 100 ml. Hexane (150 ml) was added. The mixture was shaken for 5 min. and the supernatant was decanted. The residue was dried to give a yellow solid (36.8 g, 90%).

出典