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    64183-27-3

    Catalog No. EBD15232

    CAS 64183-27-3

    Name (2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol

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    Basic Information

    Synonyms: 2'-Fluoro-2'-deoxyadenosine (2R,3R,4R,5R)-5-(6-Aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol 2'-deoxy-2'-fluoroadenosine 9-(2-deoxy-2-fluoropentofuranosyl)-9H-purin-6-amine (2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol

    Molecular Formula: C10H12FN5O3

    Molecular Weight: 269.23

    MDL Number: MFCD09750859

    Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides

    Product Description:
    2'-Fluoro-2'-deoxyadenosine is a fluorinated nucleoside analog. Its structure features a fluorine atom at the 2' position of the ribose sugar ring, replacing the hydroxyl group found in the natural nucleoside deoxyadenosine. This modification significantly alters its biochemical properties and metabolic stability. This compound is primarily investigated as a potential antiviral and anticancer agent. As a nucleoside analog, it can be phosphorylated intracellularly to its active triphosphate form, which may then be incorporated into growing DNA or RNA chains by viral or cellular polymerases, leading to chain termination and inhibition of nucleic acid synthesis. It has been studied in the context of inhibiting viral replication, particularly for viruses like hepatitis B virus (HBV). The introduction of the 2'-fluoro substituent enhances the molecule's resistance to degradation by cellular nucleases compared to its non-fluorinated counterpart, potentially improving its pharmacokinetic profile. Research on this compound contributes to the development of novel therapeutic nucleosides for treating viral infections and certain types of cancer.
    Physical Properties

    Boiling Point: 628.6 °C at 760 mmHg

    Flash Point: 334 °C

    Density: 2.01 g/cm3

    mg g kg ml l t