trans-1-(3-Oxoprop-1-enyl)thymine

Base Information

• Chemical Name: trans-1-(3-Oxoprop-1-enyl)thymine
• CAS No.: 79251-82-4
• Molecular Formula: C₈H₈N₂O₃
• Molecular Weight: 180.163
• Mol file: 79251-82-4.mol

Synonyms:trans-1-(3-Oxoprop-1-enyl)thymine

Chemical Property of trans-1-(3-Oxoprop-1-enyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-1-(3-Oxoprop-1-enyl)thymine

There total 8 articles about trans-1-(3-Oxoprop-1-enyl)thymine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 33.0%

C23H33(2)HN2O9S2Si (1262528-37-9) → (E)-3-(thymin-3-yl)propenal (1241784-84-8) + C19H20(2)H2N2O10S2 + trans-1-(3-Oxoprop-1-enyl)thymine (79251-82-4,85394-19-0) + thymin (65-71-4,28806-14-6,691841-57-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2010.06.039

Reference yield:

1-<<<2-(Acetyloxy)acetyl>oxy>-3-oxopropyl>thymine (130859-95-9) → Malondialdehyde (542-78-9) + trans-1-(3-Oxoprop-1-enyl)thymine (79251-82-4,85394-19-0) + thymin (65-71-4,28806-14-6,691841-57-3)

Guidance literature:

With water; at 25 ℃; Product distribution; Mechanism; Rate constant; effect of pH;

DOI:10.1021/jo00001a011

Reference yield:

1-((2R,4S,5S)-5-Hydroperoxy-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione → glycolic Acid (79-14-1) + trans-1-(3-Oxoprop-1-enyl)thymine (79251-82-4,85394-19-0)

Guidance literature:

With sodium phenyl phosphate; In [D₃]acetonitrile; water-d2; at 20 ℃; Mechanism; other hydroperoxymononucleosides;

DOI:10.1021/ja00127a038

upstream raw materials:

1-<<<2-(Acetyloxy)acetyl>oxy>-3-oxopropyl>thymine

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

Propargylic aldehyde

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

Refernces

• 1、 Sugden, Kent D.,Wetterhahn, Karen E.. "Identification of the oxidized products formed upon reaction of Chromium(V) with thymidine nucleotides". . p. 10811 - 10818. Retrieved 2007/10/03.
• 2、 McGall, Glenn H.,Stubbe, JoAnne,Kozarich, John W.. "Acyl Migration in the Production of Thymine Propenal from 3'-O-Benzoyl-5'-deoxy-4'-hydroperoxythymidine: A Reinterpretation of a Putative Model for Bleomycin-Mediated DNA Degradation". . p. 48 - 55. Retrieved 2007/10/02.