Reaktion #342103

Reaktionsgleichung

Compound 114

5′-O-tert-Butyldiphenylsilyl-2′-O-(2-methoxyethyl)-4′-thio-uridine

Acetic acid

→

Compound 51

Ausbeute 83.0%

2′-O-(2-Methoxyethyl)-4′-thio-uridine

Ausbeute 83.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting reaction mixture
2. 2
   SonstigeThe solvent was removed under reduced pressure
3. 3
   Sonstigethe residue obtained
4. 4
   Sonstigewas purified by flash silica gel column chromatography
5. 5
   Wascheneluted with acetone

Vorschrift

To a solution of Compound 114 (0.49 g, 0.88 mmol) in anhydrous THF (37 mL) 1M tetrabutylammonium fluoride in THF (1.8 mL) was added. Acetic acid (0.12 mL, 2.03 mmol) was added to this mixture and the resulting reaction mixture stirred at room temperature for 30 min. The solvent was removed under reduced pressure and the residue obtained was purified by flash silica gel column chromatography and eluted with acetone to yield Compound 51 (0.23 g, 83%). 1H NMR (300 MHz, DMSO-d6): 11.2 (s, 1H), 8.04 (d, 1H,), 5.94 (d, 1H), 5.69 (d, 1H), 5.20 (d, 1H), 4.15 (t, 1H), 4.04 (m, 1H), 3.67-3.53 (m, 6H), 3.47-3.36 (m, 2H), 3.31 (s, 3H); MS (API-ES) m/z 341.0 [M+Na]+.

Quelle