Réaction #417953

Équation de réaction

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

→

( 27 )

Rendement 61.3%

4′-azido-2′-deoxy-2′-fluoroguanosine

Rendement 61.3%

Solvants

HCOOH

Conditions de réaction

Traitement

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

Mode opératoire

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]+.

Source