5'-DEOXYTHYMIDINE

Base Information

• Chemical Name: 5'-DEOXYTHYMIDINE
• CAS No.: 3458-14-8
• Molecular Formula: C10H14 N2 O4
• Molecular Weight: 226.232
• Mol file: 3458-14-8.mol

Synonyms:Uridine,2',5'-dideoxy-5-methyl- (8CI); 2',5'-Dideoxy-5-methyluridine;5-Methyl-2',5'-dideoxyuridine; 5'-Deoxythymidine

Chemical Property of 5'-DEOXYTHYMIDINE

Chemical Property:

• Melting Point: 192-193 °C(lit.)
• Boiling Point: °Cat760mmHg
• PKA: 9.55±0.10(Predicted)
• Flash Point: °C
• PSA: 84.32000
• Density: 1.344g/cm³
• LogP: -0.48670
• Storage Temp.: −20°C
• Solubility.: ≤10mg/ml in DMSO;16mg/ml in dimethyl formamide

Purity/Quality:

97% ^*data from raw suppliers

5''-Deoxythymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The pyrimidine thymidine consists of thymine combined with deoxyribose. Prior to polymerization into DNA, thymidine must be phosphorylated at the hydroxyl group on carbon 5 of the ribose moiety. 5'-Deoxythymidine is a form of thymidine in which the hydroxyl group on carbon 5 of ribose has been replaced with hydrogen. As a result, 5'-DEOXYTHYMIDINE cannot be phosphorylated and used by DNA polymerase in the synthesis of DNA. 5'-Deoxythymidine is readily imported by cellular nucleoside importers and competitively inhibits the influx of thymidine. It demonstrates antibacterial activity against B. subtilis and S. aureus.[Cayman Chemical]

Technology Process of 5'-DEOXYTHYMIDINE

There total 8 articles about 5'-DEOXYTHYMIDINE 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: 88.0%

5’-chloro-5’-deoxythymidine (25905-50-4) → 5'-deoxythymidine (3458-14-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; for 18h; Heating;

DOI:10.1080/15257779508009485

Reference yield: 42.0%

5’-bromo-5’-deoxythymidine (25905-51-5) → 5'-deoxythymidine (3458-14-8)

Guidance literature:

With air; triethyl borane; bis[4-(2-hydroxyethoxy)phenyl]silane; In tetrahydrofuran; water; at 20 ℃; for 4h;

DOI:10.1246/bcsj.70.2519

Reference yield: 35.0%

5'-O-(phenoxythiocarbonyl)thymidine (123884-10-6) → 5'-deoxythymidine (3458-14-8) + 6,5'-cyclo-5'-deoxy-5,6-dihydrothymidine (123884-11-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 1.5h; Heating;

DOI:10.1021/jo00290a024

upstream raw materials:

1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

5'-O-(phenoxythiocarbonyl)thymidine

5’-chloro-5’-deoxythymidine

5’-bromo-5’-deoxythymidine

Downstream raw materials:

2',5'-dideoxy-5-fluorouridine

thymin

6-Methyluracil