TFA-ap-dC Chemical Properties

Density 

1.65±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.24±0.46(Predicted)

Appearance

White to yellow Solid

TFA-ap-dC Usage And Synthesis

Synthesis

Under argon protection, 5-iodo-2'-deoxycytidine (10 g, 28.32 mmol) was dissolved in DMF (200 mL) in a light protected round bottom flask. CuI (1.08 g, 5.67 mmol), triethylamine (7.80 mL, 55.60 mmol), 2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide (12.8 g, 84.76 mmol), and Pd(PPh3)4 (3.27 g, 2.83 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 18 hours. Subsequently, sodium bicarbonate (20 mg) was added and stirring was continued for 1 hour. After completion of the reaction, the crude product was obtained by filtration under reduced pressure and concentration to remove the volatile solvent. Purification by silica gel fast column chromatography (elution gradient: CH2Cl2, CH2Cl2:EtOAc 1:1, EtOAc:MeOH 9:1) afforded the target compound N-(3-(4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuryl-2- yl)-2-oxo-1,2-dihydropyrimidin-5-yl)propane- 2-yn-1-yl)-2,2,2-trifluoroacetamide (7) as a beige solid in quantitative yield.1H NMR (D2O) δ 2.24-2.17 (m, 1H, H-2'), 2.41-2.37 (m, 1H, H-2'), 3.68 (dd, J = 12.5, 5.0 Hz, 1H, H-5'), 3.77 (dd, J = 12.5, 3.2 Hz, 1H, H-5'), 3.99 (m, 1H, H-4'), 4.27 (s, 2H, CH2N), 4.34 (m, 1H, H-3'), 6.11 (t, J = 6.3 Hz, 1H, H-1'), 8.1 (br s, 1H, NH); MS (ES): m/z (%) (M-H) 375 (100).

References

[1] Patent: EP2607369, 2015, B1. Location in patent: Paragraph 0138
[2] Chemical Communications, 2005, # 36, p. 4551 - 4553
[3] Patent: WO2016/182984, 2016, A1. Location in patent: Paragraph 00140
[4] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15071 - 15082
[5] Patent: CN104693258, 2017, B. Location in patent: Paragraph 0088; 0094; 0095

TFA-ap-dC(115899-38-2)Related Product Information

• TFA-ap-dU
• TFA-aa-dC
• 7-DEAZA-7-IODO-2'-DEOXYADENOSINE
• 7-DEAZA-7-IODO-2'-DEOXYGUANOSINE
• 2',3'-DIDEOXYADENOSINETRIPHOSPHORICACID=DDATP
• 2',3'-dideoxycytidine 5'-triphosphate