16053-52-4

Basic information

• Product Name: 1-(2'-deoxy-beta-threopentofuranosyl)thymine
• Synonyms: 1-(2'-deoxy-beta-threopentofuranosyl)thymine;1-((2R,4R,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione;1-(2-Deoxy--D-xylofuranosyl)-5-methyluracil;1-(2-Deoxy-β-D-threo-pentofuranosyl)-5-methyluricil;1-(2-Deoxy-β-D-threopentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione;Zidovudine impurity M;1-(2-Deoxy-beta-D-xylofuranosyl)-5-methyluracil
• CAS NO: 16053-52-4
• Molecular Formula: C₁₀H₁₄N₂O₅
• Molecular Weight: 242.22856
• Mol File: 16053-52-4.mol
• Article Data: 35

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.452g/cm³
• CAS DataBase Reference: 1-(2'-deoxy-beta-threopentofuranosyl)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2'-deoxy-beta-threopentofuranosyl)thymine(16053-52-4)
• EPA Substance Registry System: 1-(2'-deoxy-beta-threopentofuranosyl)thymine(16053-52-4)

Safety Data

• Hazardous Substances Data: 16053-52-4(Hazardous Substances Data)

Usage

Description

1-(2'-deoxy-beta-threopentofuranosyl)thymine, also known as 3'-β-Thymidine (Stavudine EP Impurity B), is a chemical compound that serves as an intermediate in the production of fluorothymidine and phosphorylase derivatives. It plays a significant role in the synthesis of antiviral agents and has applications in various fields due to its unique properties.

Uses

Used in Pharmaceutical Industry:
1-(2'-deoxy-beta-threopentofuranosyl)thymine is used as an intermediate for the production of antiviral agents, specifically for the synthesis of Stavudine. Stavudine is an antiviral drug that acts as a reverse transcriptase inhibitor, which is crucial in the treatment of viral infections, particularly Human Immunodeficiency Virus (HIV).
Additionally, 1-(2'-deoxy-beta-threopentofuranosyl)thymine is used in the development of other antiviral medications that target reverse transcriptase, an enzyme essential for the replication of certain viruses. By inhibiting this enzyme, the compound helps in preventing the spread of the virus and managing the progression of the disease.

Upstream product

• 237060-98-9 2',3',5'-tri-O-benzoyl-5-methyl-L-uridine 
• 271248-28-3 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-L-thymidine 
• 793716-98-0 3',5'-di-O-levulinoyl-β-L-thymidine 
• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 65-71-4 thymin 
• 26879-47-0 1-(β-L-ribofuranosyl)thymine 
• 271248-26-1 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-5-methyl-L-uridine 
• 271248-27-2 3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-5-methyl-2'-O-(phenoxythiocarbonyl)-L-uridine 
• 7791-71-1 5'-O-tritylthymidine 
• 3056-13-1 1-(2-deoxy-3,5-di-p-toluoyl-β-L-ribose)-5-methyluracil 
• 40093-95-6 1-(3′,5′-di-O-benzoyl-2′-deoxy-αβ-L-ribofuranosyl)thymine 
• 817622-48-3 C₂₀H₃₀N₂O₇ 
• 143156-51-8 C₁₂H₁₈N₂O₆ 
• 1062488-85-0 C₂₆H₂₆N₂O₇ 

Downstream Products

• 131607-27-7 1-((2S,4R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 207128-15-2 Methanesulfonic acid (2S,3R,5S)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 207128-17-4 1-((2S,4S,5S)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 207128-19-6 1-((2S,4R,5S)-4-Fluoro-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 52417-09-1 3'-O-(4,4'-dimethoxytriphenylmethyl)-5'-O-fluorenylmethoxycarbonylthymidine 
• 1333995-40-6 C₂₁H₂₄ClN₈O₆P 
• 1333995-50-8 C₂₁H₂₆N₉O₆P 
• 1333995-78-0 C₂₁H₂₅ClN₉O₆P 
• 1333995-93-9 C₂₁H₂₇N₁₀O₆P 
• 1333996-11-4 C₂₁H₂₇N₆O₈P 
• 132979-39-6 1-(3-azido-2,3-dideoxy-β-L-erythro-pentofuranosyl)thymine 
• 1356470-37-5 3',5'-di-O-acetyl-5-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)methyl)-2'-deoxy-β-L-uridine 
• 1356470-38-6 5-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)methyl)-2'-deoxy-β-L-uridine 

Relevant articles and documents

Synthesis and evaluation of 3′-[18F]fluorothymidine-5′-squaryl as a bioisostere of 3′-[18F]fluorothymidine-5′-monophosphate

The squaryl moiety has emerged as an important phosphate bioisostere with reportedly greater cell permeability. It has been used in the synthesis of several therapeutic drug molecules including nucleoside and nucleotide analogues but is yet to be evaluated in the context of positron emission tomography (PET) imaging. We have designed, synthesised and evaluated 3′-[18F]fluorothymidine-5′-squaryl ([18F]SqFLT) as a bioisostere to 3′-[18F]fluorothymidine-5′-monophosphate ([18F]FLTMP) for imaging thymidylate kinase (TMPK) activity. The overall radiochemical yield (RCY) was 6.7 ± 2.5% and radiochemical purity (RCP) was >90%. Biological evaluationin vitroshowed low tracer uptake (?1) but significantly discriminated between wildtype HCT116 and CRISPR/Cas9 generated TMPK knockdown HCT116shTMPK?. Evaluation of [18F]SqFLT in HCT116 and HCT116shTMPK?xenograft mouse models showed statistically significant differences in tumour uptake, but lacked an effective tissue retention mechanism, making the radiotracer in its current form unsuitable for PET imaging of proliferation.

Radiosynthesis of [18F]-labelled pro-nucleotides (ProtIDes)

Phosphoramidate pro-nucleotides (ProTides) have revolutionized the field of anti-viral and anti-cancer nucleoside therapy, overcoming the major limitations of nucleoside therapies and achieving clinical and commercial success. Despite the translation of P

Method for preparing high-purity telbivudine compound

The invention belongs to the technical field of medicine and provides a method for preparing a high-purity telbivudine compound. The method includes the steps that an LTD-4 compound serves as the raw material and reacts with thymine subjected to silicification protection, and an intermediate, namely an LTD-5 compound, can be obtained; then, through deprotection reaction, the telbivudine compound is obtained after post-processing, wherein MeONa serves as an alkaline reagent of the deprotection reaction, and strong-acidity resin serves as a dealkalization reagent. The method simplifies the production process, the yield of each step is high, and a target product high in purity and yield is obtained. Please see the structural formula in the description.