CAS 15981-92-7

2,3'-anhydrothymidine

Description:

2,3'-Anhydrothymidine is a nucleoside analog derived from thymidine, characterized by the absence of the hydroxyl group at the 2' and 3' positions of the sugar moiety. This modification imparts unique properties to the compound, making it of interest in biochemical and pharmaceutical research. The structure consists of a pyrimidine base (thymine) linked to a sugar (deoxyribose) that has undergone dehydration. As a result, 2,3'-anhydrothymidine exhibits increased stability against nucleophilic attack, which can enhance its potential as an antiviral or anticancer agent. The compound is typically white to off-white in appearance and is soluble in polar solvents. Its mechanism of action often involves interference with nucleic acid synthesis, making it a valuable tool in studying DNA replication and repair processes. Additionally, its structural similarity to natural nucleosides allows it to be incorporated into nucleic acids, providing insights into the effects of modified nucleotides on biological systems. Overall, 2,3'-anhydrothymidine serves as a significant compound in the field of medicinal chemistry and molecular biology.

Formula: C₁₀H₁₂N₂O₄

InChI: InChI=1/C10H12N2O4/c1-5-3-12-8-2-6(7(4-13)15-8)16-10(12)11-9(5)14/h3,6-8,13H,2,4H2,1H3/t6-,7+,8+/m0/s1

Synonyms:

• 2,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-
• 2,3'-O-Cyclothymidine
• 2,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-
• AHT
• Anhydrothymidine
• Nsc 144601
• O2,3'-Cyclothymidine
• 3-(hydroxymethyl)-8-methyl-2,3-dihydro-9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-9-one
• (2R,3R,5R)-3-(hydroxymethyl)-8-methyl-2,3-dihydro-9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-9-one
• (2S,3R,5R)-3-(hydroxymethyl)-8-methyl-2,3-dihydro-9H-2,5-methanopyrimido[2,1-b][1,5,3]dioxazepin-9-one
• Anhydro-T

2,3''-Anhydrothymidine

CAS: 15981-92-7

Formula: C₁₀H₁₂N₂O₄

Molecular weight: 224.21

Ref: 7W-GN9946

2,3'-Anhydrothymidine

CAS: 15981-92-7

2,3'-Anhydrothymidine is a Nucleoside Derivative - Anhydro-nucleoside.

Formula: C₁₀H₁₂N₂O₄

Color and Shape: Solid

Molecular weight: 224.21

Ref: TM-TNU1139

2,3’-Anhydrothymidine

Controlled Product

CAS: 15981-92-7

Applications An intermediate in the preparation of thymidine derivatives
References el Kouni, M., et al.: Biochem. Pharmacol., 51, 1687 (1996),

Formula: C₁₀H₁₂N₂O₄

Color and Shape: Neat

Molecular weight: 224.21

Ref: TR-A656500

2,3'-Anhydrothymidine

CAS: 15981-92-7

2,3'-Anhydrothymidine is a piperidine-containing nucleoside analog that inhibits the replication of HIV and other viruses. It is structurally related to acyclovir, but has an increased resistance to viral inactivation by acyclovir-resistant strains. 2,3'-Anhydrothymidine binds to the ribose sugar of the viral nucleic acid and prevents the formation of a covalent bond between the 5' hydroxyl group of ribose and the 3' phosphate group. It also inhibits protein synthesis by interfering with the incorporation of amino acids into proteins. 2,3'-Anhydrothymidine has been shown to be effective against human immunodeficiency virus type 1 (HIV-1) in animal models and clinical studies.

Formula: C₁₀H₁₂N₂O₄

Purity: Min. 95%

Color and Shape: White Powder

Molecular weight: 224.21 g/mol

Ref: 3D-NA04576

2,3’-Anhydrothymidine-d3

Controlled Product

CAS: 15981-92-7

Applications: An intermediate in the preparation of labelled thymidine derivatives
References el Kouni, M., et al.: Biochem. Pharmacol., 51, 1687 (1996),

Formula: C₁₀D₃H₉N₂O₄

Color and Shape: Neat

Molecular weight: 227.232

Ref: TR-A656502