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| | 2'-Fluoro-2'-deoxyuridine Basic information |
| | 2'-Fluoro-2'-deoxyuridine Chemical Properties |
| Melting point | 147.0 to 153.0 °C | | density | 1.63±0.1 g/cm3(Predicted) | | refractive index | 53 ° (C=0.3, H2O) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Soluble in methanol. | | pka | 9.39±0.10(Predicted) | | form | Powder | | color | White to Off-white | | Optical Rotation | α20/D +53°±3°, c = 0.3 in water | | Water Solubility | soluble in water | | InChI | InChI=1S/C9H11FN2O5/c10-6-7(15)4(3-13)17-8(6)12-2-1-5(14)11-9(12)16/h1-2,4,6-8,13,15H,3H2,(H,11,14,16)/t4-,6-,7-,8-/m1/s1 | | InChIKey | UIYWFOZZIZEEKJ-XVFCMESISA-N | | SMILES | OC[C@H]1O[C@@H](N2C=CC(=O)NC2=O)[C@H](F)[C@@H]1O | | CAS DataBase Reference | 784-71-4(CAS DataBase Reference) |
| | 2'-Fluoro-2'-deoxyuridine Usage And Synthesis |
| Description | 2'-Deoxy-2'-fluorouridine is a nucleoside analog that inhibits the replication of wild-type viruses by binding to the viral RNA. 2'-Deoxy-2'-fluorouridine has been shown to inhibit the replication of resistant mutants in vitro, and this inhibition can be reversed by increasing the concentration of 2'-deoxy-2'-fluorouridine. 2'-Deoxy-2'-fluorouridine also binds to duplexes of dsDNA with high affinity and specificity. | | Chemical Properties | White to almost white crystalline powder | | Uses | 2'-Fluoro-2'-deoxyuridine is used as a component incorporated into therapeutic oligonucleotides to combat prostate and breast cancer. | | Uses | A component incorporated into therapeutic oligonucleotides to combat prostate and breast cancer. | | Synthesis | Method for the synthesis of 2'-Fluoro-2'-deoxyuridine, comprising the following steps:
(1) Uridine, diphenyl carbonate was added in dimethylformamide, dissolved at elevated temperature, the solution was clarified, the catalyst sodium bicarbonate was added under the condition of maintaining temperature, the reaction was carried out at elevated temperature for the second time, the reaction was completed, the temperature was cooled down naturally to room temperature, stirred, filtered, and the cake was dried to obtain compound 2.
(2) Compound 2, anhydrous potassium fluoride, catalyst boron trifluoride ethyl ether dissolved in a solvent, temperature rise reaction, after the completion of the reaction, filtration and concentration, to obtain 2'-fluoro-2'-deoxyuridine.
However, the hydroxyl conversion rate of this method is low, 2'-fluoro-2'-deoxyuridine is an extremely viscous compound, and it cannot be cured and purified when the purity is not high, resulting in the need for the method to be purified by passing through a column at a later stage, and it cannot be used in a factory for continuous and scaled-up production.
| | References | [1] Nucleosides, Nucleotides and Nucleic Acids, 2018, vol. 37, # 4, p. 232 - 247 |
| | 2'-Fluoro-2'-deoxyuridine Preparation Products And Raw materials |
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