Reacción #439207

Ecuación de reacción

MeOH

5′-O-tert-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine

Triethylamine trihydrofluoride

→

2′-O-(dimethylaminooxyethyl)-5-methyluridine

Rendimiento 92.5%

Disolventes

CH2Cl2

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed under vacuum
2. 2
   Otrothe residue purified by flash column chromatography (eluted with 10% MeOH in CH2Cl2)

Procedimiento

Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and TEA (1.67 mL, 12 mmol, dry, stored over KOH) and added to 5′-O-tert-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol). The reaction was stirred at room temperature for 24 hrs and monitored by TLC (5% MeOH in CH2Cl2). The solvent was removed under vacuum and the residue purified by flash column chromatography (eluted with 10% MeOH in CH2Cl2) to afford 2′-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%) upon rotary evaporation of the solvent.

Fuente