2'-Deoxy-5'-O-DMT-2'-fluorouridine Chemical Properties

Density 

1.38±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

9.39±0.10(Predicted)

form 

Powder

color 

White to Pale Yellow

InChIKey

CSSFZSSZXOCCJB-MNBKXICWNA-N

SMILES

N1(C=CC(=O)NC1=O)[C@@H]1O[C@H](COC(C2=CC=CC=C2)(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)[C@@H](O)[C@H]1F |&1:8,10,36,38,r|

Safety Information

HS Code 

2934999090

2'-Deoxy-5'-O-DMT-2'-fluorouridine Usage And Synthesis

Uses

2'-Deoxy-5'-O-DMT-2'-fluorouridine, a nucleoside analogue, is a 5’-O-DMTr-5-FUDR derivative with potent anti-yellow fever (YFV) activity[1].

Definition

2'-Deoxy-5'-O-DMT-2'-fluorouridine, a nucleoside analogue, is a 5’-O-DMTr-5-FUDR derivative with potent anti-yellow fever (YFV) activity.

Biological Activity

2'-Deoxy-5'-O-DMT-2'-fluorouridine (compound 15h) has 100% inhibition against YFV at 20 mM. 2'-Deoxy-5'-O-DMT-2'-fluorouridine proves to be noncytotoxic at concentrations up to 20 mM.

Synthesis

2'-Deoxy-2'-fluorouridine (3.00 g, 12.2 mmol) was dissolved in anhydrous pyridine, and the decompression concentration operation was repeated three times to achieve dehydration azeotropic distillation. Subsequently, the reaction mixture was dissolved in anhydrous pyridine (120 mL) under argon protection, 4,4'-dimethoxytrityl chloride (4.55 g, 13.4 mmol) was added, and the reaction was stirred for 3 hours at room temperature. After completion of the reaction, ethyl acetate (150 mL) and water (60 mL) were added to the reaction mixture and layered. The organic layer was washed sequentially with 5% aqueous sodium bicarbonate (20 mL x 3), water (20 mL) and saturated saline (20 mL), followed by drying with anhydrous sodium sulfate. After filtration, the solvent was removed by evaporation and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 50:50 to 0:100 (v/v) containing 1% triethylamine). The fraction containing the target product was collected and concentrated to give 1-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (8.48 g, quantitative yield).

References

[1] Christopher McGuigan, et al. Anti-flavivirus Activity of Different Tritylated Pyrimidine and Purine Nucleoside Analogues. ChemistryOpen. 2016 Jan 21;5(3):227-35. DOI:10.1002/open.201500216

2'-Deoxy-5'-O-DMT-2'-fluorouridine(146954-74-7)Related Product Information

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