TFA-ap-dU Chemical Properties

Melting point:

>116°C (dec.)

Density 

1?+-.0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

8.17±0.10(Predicted)

form 

Solid

color 

Pale Yellow to Light Orange

TFA-ap-dU Usage And Synthesis

Uses

2''-Deoxy-5-[3-[(2,2,2-trifluoroacetyl)amino]-1-propyn-1-yl]uridine is an intermediate in the synthesis of fluorescent labeling compounds of cyclooctyne-modified deoxyuridine triphosphates in DNA.

Synthesis

To a solution of 5-iodouridine (5.0 g, 14.1 mmol) in anhydrous DMF (40 mL), CuI (0.20 g, 1.05 mmol) and Pd(PPh3)4 (0.41 g, 0.35 mmol) were added under nitrogen protection. After stirring for 10 min, triethylamine (4.0 mL, 28.6 mmol) and 2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide (5.4 g, 35.7 mmol) were added sequentially and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, all volatiles were removed under vacuum and the residue was purified by rapid chromatography on silica gel [eluent: EtOAc/MeOH (0-15%)] to afford the target product 2,2,2-trifluoro-N-(3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4- (tetrahydropyrimidin-5-yl)prop-2-ynyl)acetamide as a yellow solid (4.1 g, 76% yield).1H-NMR (DMSO-d6) δ: 11.68 (br s, 1H, NH), 10.02 (s, 1H, NH), 7.94 (s, 1H, H-6), 6.11 (t, J = 7.2 Hz, H-1'), 5.29 (d, J = 0.4 Hz, NH), 6.11 (t, J = 0.4 Hz, NH), 5.29 (d, J = 0.4 Hz, NH). J = 0.4 Hz, 1H, OH), 4.21 (m, 3H, H-3', NCH2), 3.71-3.83 (m, 2H, CH2-5'), 2.15-2.19 (m, 1H, H-2'), 2.03-2.08 (m, 1H, H-2'). Mass Spectra (ESI): Calculated value C14H14F3N3O6 (M + Na)+ 400, measured value 400.

References

[1] Tetrahedron, 2009, vol. 65, # 4, p. 934 - 939
[2] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15071 - 15082
[3] Helvetica Chimica Acta, 2007, vol. 90, # 6, p. 1082 - 1098
[4] Journal of the American Chemical Society, 2011, vol. 133, # 8, p. 2463 - 2480
[5] Helvetica Chimica Acta, 2008, vol. 91, # 1, p. 165 - 175

TFA-ap-dU(115899-40-6)Related Product Information

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