Reaktion #417953

Reaktionsgleichung

4′-Azido-2′-fluoro-N2-(4-methoxytrityl)-2′-deoxyguanosine

→

( 27 )

Ausbeute 61.3%

4′-azido-2′-deoxy-2′-fluoroguanosine

Ausbeute 61.3%

Lösungsmittel

HCOOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated at R.T. and co-evaporated with MeOH/toluene (3 times)
2. 2
   SonstigePurification

Vorschrift

Compound (27)—A solution of compound 50-8 (580 mg, 0.72 mmol) in 7N NH3 in CH3OH (30 mL) was stirred at R.T. overnight. The solvent was evaporated in vacuo, and the residue was purified on silica gel column using DCM/MeOH (95:5 to 90:10) to give 4′-azido-2′-fluoro-N2-(4-methoxytrityl)-2′-deoxyguanosine (332 mg, 77%). 4′-Azido-2′-fluoro-N2-(4-methoxytrityl)-2′-deoxyguanosine (80 mg, 0.13 mmol) was dissolved in 80% HCOOH (3 mL), stirred at R.T. for 3 hours. The solvent was evaporated at R.T. and co-evaporated with MeOH/toluene (3 times). Purification using RP-HPLC (water:acetonitrile) gave (27) (26.0 mg, 61%) as a white foam after lyophilization. 1H NMR (DMSO-d6) δ 3.55-3.67 (m, 2H), 4.69-4.77 (m, 1H), 5.37 (dd, J=2.4, 4.8 Hz, 1H), 5.51 (t, J=2.8 Hz, 1H), 5.65 (t, J=6.0 Hz, 1H), 6.13 (d, J=7.6 Hz, 1H), 6.30 (dd, J=2.4, 18.4 Hz, 1H), 6.60 (br s, 1H), 7.91 (s, 1H), 10.74 (br s, 1H); 19F NMR δ (−199.0 to −199.25, m); ESI-LCMS m/z=325.3 [M+H]+.

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