59495-22-6

Basic information

• Product Name: O(4)-ethylthymidine
• Synonyms: O(4)-ethylthymidine
• CAS NO: 59495-22-6
• Molecular Formula: C₁₂H₁₈N₂O₅
• Molecular Weight: 270.283
• Mol File: 59495-22-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 452.8°C at 760 mmHg
• Flash Point: 227.6°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 4.22E-10mmHg at 25°C
• Refractive Index: 1.607
• CAS DataBase Reference: O(4)-ethylthymidine(CAS DataBase Reference)
• NIST Chemistry Reference: O(4)-ethylthymidine(59495-22-6)
• EPA Substance Registry System: O(4)-ethylthymidine(59495-22-6)

Safety Data

• Hazardous Substances Data: 59495-22-6(Hazardous Substances Data)

Usage

Uses

O4-Ethylthymidine is known to be highly mutagenic and persistent in mammalian tissues

InChI:InChI=1/C12H18N2O5/c1-3-18-11-7(2)5-14(12(17)13-11)10-4-8(16)9(6-15)19-10/h5,8-10,15-16H,3-4,6H2,1-2H3/t8-,9+,10+/m0/s1

Upstream product

• 64-17-5 ethanol 
• 80991-41-9 1-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone 
• 141-52-6 sodium ethanolate 
• 6979-97-1 3',5'-diacetylthymidine 
• 50-89-5 thymidine 
• 80991-40-8 1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tertbutyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one 
• 137121-87-0 α/β-D-thymidine 

Downstream Products

• 99268-61-8 3',5'-bis(O-pentafluorobenzyl)-O⁴-ethylthymidine 
• 117775-85-6 5'-O-(4,4'-dimethoxytrityl)-O⁴-ethylthymidine 

Relevant articles and documents

Pentafluorobenzylation of O4-ethylthymidine and analogues by phase-transfer catalysis for determination by gas chromatography with electron capture detection.

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Solid-phase synthesis of oligonucleotides containing 4-alkoxythymidine residues

Immobilized and fully protected oligodeoxynucleotides containing a 4-(1,2,4-triazolyl)thymidine residue at a predetermined position were prepared according to a well-established phosphite triester methodology using 2-cyanoethyl phosphoramidites of a 4-(1,2,4-triazolyl)-substituted thymidine and standard protected nucleosides.Treatment of the immobilized oligomer with methanol, ethanol or n-propanol in the presence of DBU at 50 deg C gave the corresponding oligonucleotides containing 4-methoxy, 4-ethoxy or 4-n-propoxythymidine residue.

Carcinogenic Alkylation of Nucleic Acid Bases. Structure and Conformation of O4-Ethyl-2'-deoxythymidine in the Solid State and in Solution

O4-Ethyl-2'-deoxythymidine (e4dT) crystallizes in the monoclinic space group P21, and the cell dimensions are a = 5.079(1) Angstroem, b = 15.054(1) Angstroem, c = 8.467(1) Angstroem, β = 94.07(1) deg.X-ray intensity data were measured with a diffractometer, and the structure was solved by direct methods.Least-squares refinement, which included all hydrogen atoms; converged at R = 0.030 for 1365 observed reflections.The O-ethyl group is coplanar with the pyrimidine ring, the methylene carbon atom being syn to N3.It is shown that O4-alkylation causes significant changes in the geometry of the ring which can be attributed to an altered electronic structure.The conformation about the glycosidic bond is anti with χCN = 22.8 deg.The deoxyribose ring dopts the unusual C3' endo/C2' exo twist pucker, and the gauche(1+) rotamer of the CH2OH side chain is stabilized by an intramolecular C6-H...O5' hydrogen bond.Proton NMR data for e4dT and e4dU reveal the usual preference for the C2' endo sugar pucker and a conformer distribution for the C4'-C5' bond which is expected for 2'-deoxyribosides.Comments are made on the relevance of the structure to base mispairing of O-alkyl pyrimidines and their enzymatic repair.