L-Phenylalanine, methyl ester → 3-Azido-3-deoxythymidine 5-methoxy-L-phenylalaninylphosphoramidate

Beteiligte Stoffe

Reaktionsschritte

Compound 40 (277 mg, 0.640 mmol) and phenylalanine methyl ester (HCl salt, 276 mg, 1.28 mmol) were subjected to a procedure similar to that described in Example 6. Flash chromatography (SiO2, 5:2:0.25 CHCl3/MeOH/H2O containing 0.5% conc. NH4OH) gave the title compound (216 mg, 64%) as a white solid. 1H NMR (D2O, 300 MHz) 7.424 (s, 1H), 7.120-6.974 (m, 5H), 5.998 (t, J=6.7 Hz, 1H), 4.153 (m, 1H), 3.843 (m, 1H), 3.728 (m, 1H), 3.585 (m, 2H), 3.491 (s, 3H), 2.794 (m, 1H), 2.699 (m, 1H), 2.219 (m, 1H), 2.116 (m, 1H), 1.675 (s, 3H); 31P NMR (D2O, 121 MHz) 6.370; HRMS (FAB m/z calcd for C13H20N6O8P (M+H)+ 419.1080, found 419.1103.

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