52486-19-8

Usage

Chemical Class

Pyrimidine nucleobase

Occurrence

Found in DNA

Chemical Structure

Pyrimidine ring with two nitrogen atoms and four carbon atoms
3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl group attached to the pyrimidine ring
5-methyl group on the pyrimidine ring

Genetic Role

Base pairing with adenine through hydrogen bonding in DNA
Essential for replication and transmission of genetic information

Biochemical Processes

Involved in DNA repair
Participates in cell signaling

Importance

Fundamental component of the molecular machinery of life

Applications

Potential use in medical research
Development of antiviral and anticancer drugs

Upstream product

• 52448-07-4 1-(2,3,5-tri-O-benzoyl-β-D-xylofuranosyl)thymine 
• 532-20-7 D-xylofuranose 
• 99018-98-1 1-(3,5-O-Isopropylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine 
• 65-71-4 2,4-dihydroxy-5-methylpyrimidine 
• 20822-87-1 1-O-acetyl-2,3,5-tri-O-benzoyl-α-D-xylofuranose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 85026-60-4 (3R,4S,5R)-4-(benzoyloxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 117257-96-2 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-xylofuranosyl)thymine 
• 42927-45-7 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose 

Downstream Products

• 22423-26-3 O-2,2'-cyclo-5-methyluridine 
• 156994-52-4 Dimethyl-carbamic acid (2R,3R,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 104218-44-2 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine 
• 190003-80-6 1-(5'-O-benzoyl-β-D-xylofuranosyl)thymine 
• 4348-54-3 1-(β-D-lyxofuranosyl)thymine 
• 50-89-5 thymidine 
• 95585-76-5 2'-bromothymidine 

Relevant academic research and scientific papers

Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation

The disclosed invention is a composition for and a method of treating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (""RT-PCR""). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

Process for the deoxygenation of nucleosides

An efficient process for the deoxygenation of 2'- and or 3'-hydroxyl groups of a nucleoside that includes reacting the hydroxyl group with 3-halopropionitrile or 2-nitroethylhalide and carbon disulfide in base to form a 2'- or 3'-(cyanoethylthio or nitroethylthio)thiocarbonyl, that is reductively eliminated and replaced with hydrogen. The deoxygenation process can be used in a wide variety of nucleoside syntheses that require the elimination of the 2'- or 3'-hydroxyl groups, including the preparation of 3'-substituted-2',3'-dideoxynucleosides such as 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine.

Discovery of a Novel Route to β-Thymidine: a Precursor for anti-AIDS Compounds

A new approach to the synthesis of β-thymidine from D-xylose is described.

Synthesis of β-D-xylofuranosyl- and 2,2'-anhydro-1-β-D-lyxofuranosylpyrimidine nucleosides

β-D-Xylofuranosylpyrimidines were obtained by condensation of silyl derivatives of pyrimidines with 1,2-di-O-acetyl-3,5-di-O-benzoyl-D-xylofuranose with subsequent deprotection of the sugar fragment.Refluxing 2-O-tosyl derivatives of nucleosides with NaI

Process for the preparation of 3'-azido-3'-deoxythymidine and intermediates

This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving: i) Conversion of D-xylose to a 2′,3′,5′-protected derivative of 1-(β-D-xylofuranosyl)thymine; ii) 2′-Deoxygenation of the xylofuranosyl thymine; and iii) 3′-Azidation of the 2′-deoxy compound.

1-(β-D-xylofuranosyl)thymine derivatives

This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving: (i) Conversion of D-xylose to a 1-(β-D-xylofuranosyl)thymine derivative; (ii) 2'-Deoxygenation of the thymine derivative; and (iii) 3'-Azidation of the 2'-deoxy compound.

Chemical process

This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving: i) Conversion of D-xylose to a 1-(β-D-xylofuranosyl)thymine derivative; ii) 2?-Deoxygenation of the thymine derivative; and iii) 3?-Azidation of the 2?-deoxy compound.

Systematic Synthesis and Biological Evaluation of α- and β-D-Xylofuranosyl Nucleosides of the Five Naturally Occurring Bases in Nucleic Acids and Related Analogues

The α- and β-D-xylofuranosyl analogues of the naturally occurring nucleosides, as well as other D-xylofuranosyl derivatives, have been the subject of a systematic synthesis and examination of their biological, i.e. antiviral antimetabolic, and cytostatic