((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol, CAS No. 4097-22-7

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4097-22-7

Catalog No. EBD28711

CAS 4097-22-7

Name ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol

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Basic Information

Synonyms: ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol 2',3'-dideoxyadenosine 2,3-Dideoxyadenosine Acerola [5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol Dideoxyadenosine DDA Adenosine,2',3'-dideoxy-

Molecular Formula: C10H13N5O2

Molecular Weight: 235.24

MDL Number: MFCD00010534

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

Product Description:

2',3'-Dideoxyadenosine (ddA, CAS 4097-22-7) is a synthetic nucleoside analogue characterized by the absence of hydroxyl groups at both the 2' and 3' positions of its ribose sugar moiety. Its chemical name is ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol. This structural modification is central to its biological activity as an antiviral agent. This compound is a key precursor and an active pharmaceutical ingredient (API) in the development of nucleoside reverse transcriptase inhibitors (NRTIs). It serves as a direct precursor to the clinically important drug didanosine (ddI, 2',3'-dideoxyinosine), which is used in the treatment of HIV-1 infection. As a chain terminator, its triphosphate form inhibits viral DNA synthesis by HIV reverse transcriptase, thereby halting viral replication. Primarily utilized in pharmaceutical research and development, 2',3'-Dideoxyadenosine is a fundamental building block in medicinal chemistry for designing antiviral therapeutics. It is also employed as a biochemical tool to study nucleotide metabolism and enzyme mechanisms. Handling requires caution in a laboratory setting due to its biological activity.

Physical Properties

Melting Point: 181-184 °C(lit.)

Boiling Point: 539.1 °C at 760 mmHg

Flash Point: 279.9 °C

Density: 1.76 g/cm3

Solubility: Soluble in water

Refractivity: -34 ° (C=1, H2O)

Storage: 2-8°C

Analytical Data

Appearance: Off-white powder