Tetrabutylammonium Fluoride → Cytidine, 2'-deoxy-5-iodo-3'-O-2-propen-1-yl-

To a stirred solution of 22 (537 mg; 1.06 mmol) in anhydrous THF (25 mL) was added 1 M TBAF in THF solution (1.17 mL; 1.17 mmol) and the reaction was stirred at room temperature for 1 h. The solvent was evaporated and the residue was dissolved in ethyl acetate (100 mL). The solution was washed by saturated aqueous NaCl and dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by flash column chromatography over silica gel using CH3OH—CH2Cl2 (1:10) as the eluent to afford 23 as white crystals (287 mg; 69% yield): 1H NMR (400 MHz, CD3OD) δ 8.47 (s, 1H, 6-H), 6.15 (dd, J=6.2, 6.7 Hz, 1H, 1′-H), 5.87-5.98 (m, 1H, CH2CH═CH2), 5.26-5.33 (dm, J=17.2 Hz, 1H, one of CH2CH═CH2), 5.14-5.19 (dm, J=10.5 Hz, 1H, one of CH2CH═CH2), 4.18 (m, 1H, 3′-H), 4.08 (m, 1H, 4′-H), 3.98-4.10 (m, 2H, CH2CH═CH2), 3.82 (dd, J=3.2, 13.0 Hz, 1H, one of 5′-H), 3.72 (dd, J=3.3, 13.0 Hz, 1H, one of 5′-H), 2.44-2.51 (ddd, J=3.2, 6.0, 13.6 Hz, 1H, one of 2′-H), 2.07-2.15 (m, 1H, one of 2′-H); 13C NMR (100 MHz, CD3OD) δ 165.4, 156.9, 148.8, 135.6, 117.0, 87.9, 86.9, 79.6, 71.2, 62.7, 57.2, 39.7; HRMS (FAB+) calcd for C12H17O4N3I (M+H+): 394.0264. Found: 394.0274.

1. customThe solvent was evaporated
2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
3. washThe solution was washed by saturated aqueous NaCl
4. dry with materialdried over anhydrous Na2SO4
5. customAfter evaporation of the solvent
6. customthe residue was purified by flash column chromatography over silica gel

ORD record

ord-0a9d4a7a847d47949c5931a9f17797af

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07982029B2