79251-82-4

Basic information

• Product Name: trans-1-(3-Oxoprop-1-enyl)thymine
• Synonyms: trans-1-(3-Oxoprop-1-enyl)thymine
• CAS NO: 79251-82-4
• Molecular Weight: 180.163
• Mol File: 79251-82-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: trans-1-(3-Oxoprop-1-enyl)thymine(CAS DataBase Reference)
• NIST Chemistry Reference: trans-1-(3-Oxoprop-1-enyl)thymine(79251-82-4)
• EPA Substance Registry System: trans-1-(3-Oxoprop-1-enyl)thymine(79251-82-4)

Safety Data

• Hazardous Substances Data: 79251-82-4(Hazardous Substances Data)

Upstream product

• 491-97-4 2-deoxythymidine diphosphate 
• 1241784-81-5 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-5-O-methanesulfonyl-α-L-threo-pentofuranosyl]thymine 
• 1262528-37-9 C₂₃H₃₃⁽²⁾HN₂O₉S₂Si 
• 90596-79-5 Benzoic acid (2S,3S,5R)-2-hydroperoxy-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 130859-95-9 1-<<<2-(Acetyloxy)acetyl>oxy>-3-oxopropyl>thymine 
• 624-67-9 Propargylic aldehyde 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 

Relevant articles and documents

Self-sacrificing acetylation observed during attempted desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-5-O-methanesulfonyl- α-l-threo-pentofuranosyl]thymine

Desilylation of 1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy- 5-O-methanesulfonyl-α-l-threo-pentofuranosyl]thymine (4) with Bu 4NF/THF, when carried out at room temperature, gave four products. Among these, there were 1-[3-O-acetyl-4-benzenesulfonyl-2-deoxy-5-O- methanesulfonyl-α-l-threo-pentofuranosyl]thymine (7) and thymine. A possible reaction mechanism is proposed, which suggests the origin of 3′-O-acetyl group of 7 and thymine as well as structures of the other two products (9a and 9b).

Cleavage of single-stranded 4′-oligonucleotide radicals in the presence of O2

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Chemistry of 4'-Hydroperoxy Nucleosides as a Model for the Intermediate in Bleomycin-Induced Degradation of DNA

The reaction of 1-(3-O-benzoyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine (5) with anhydrous hydrogen peroxide in the presence of trifluoroacetic acid gave two isomeric 4'-hydroperoxides (6 and 7).The structure of the major product was assigned as 3'-O-benzoyl-5'-deoxy-4'-hydroperoxythymine (6) on the basis of spectral data.It has been demonstrated that the 4'-hydroperoxide 6 is capable of undergoing a Criegee-type rearrangement in an aqueous buffered solution to give trans-3-(thymin-1'-yl)propenal (10) stereospecifically, whereas the more stable isomer 7 does not produce 10 under the same conditions.These model experiments suggest that once a 4'-hydroperoxy intermediate of β-D-deoxyribo configuration is formed by action of the activated bleomycin on DNA, it spontaneously decomposes to afford DNA strand scission and trans base propenal.Reduction of these 4'-hydroperoxy nucleosides with dimethyl sulfide in methanol gave thymine and γ-keto aldehyde 14 quantitatively.The result indicates that the 4'-hydroxy nucleoside might be the precursor of alkali-labile lesion in DNA.