反応 #417953

反応方程式

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

→

( 27 )

収率 61.3%

4′-azido-2′-deoxy-2′-fluoroguanosine

収率 61.3%

溶媒

HCOOH

反応条件

後処理

1. 1
   その他The solvent was evaporated at R.T. and co-evaporated with MeOH/toluene (3 times)
2. 2
   その他Purification

実験手順

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]+.

出典