Thymidine

Base Information

• Chemical Name: Thymidine
• CAS No.: 50-89-5
• Deprecated CAS: 35902-13-7
• Molecular Formula: C10H14N2O5
• Molecular Weight: 242.232
• Hs Code.: PRICE
• European Community (EC) Number: 200-070-4
• UNII: VC2W18DGKR
• DSSTox Substance ID: DTXSID5023661
• Nikkaji Number: J4.548I
• Wikipedia: Thymidine
• Wikidata: Q422464
• NCI Thesaurus Code: C880
• Pharos Ligand ID: ZPLW32L1R1P3
• Metabolomics Workbench ID: 37175
• ChEMBL ID: CHEMBL52609
• Mol file: 50-89-5.mol

Synonyms:2' Deoxythymidine;2'-Deoxythymidine;Deoxythymidine;Thymidine

Chemical Property of Thymidine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 186-188 °C(lit.)
• Refractive Index: 33 ° (C=1, 1mol/L NaOH)
• Boiling Point: 385.05°C (rough estimate)
• PKA: pK1:9.79;pK2:12.85 (25°C)
• PSA: 104.55000
• Density: 1.452 g/cm³
• LogP: -1.51430
• Storage Temp.: 0-6°C
• Solubility.: Acetone, DMSO (Slightly), Ethanol, Ethyl Acetate, Methanol (Slightly, Heated), P
• Water Solubility.: SOLUBLE
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 242.09027155
• Heavy Atom Count: 17
• Complexity: 381

Purity/Quality:

98%, ^*data from raw suppliers

Thymidine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-40-36/37/38-68
• Safety Statements: 22-24/25-37/39-26-36/37/39

MSDS Files:

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
• Recent ClinicalTrials: Treatment of TK2 Deficiency With Thymidine and Deoxycytidine
• Recent EU Clinical Trials: A phase III, open-label, randomised multicentre study to evaluate the immunogenicity and safety of a booster dose of GlaxoSmithKline Biologicals’ dTpa-IPV vaccine (Boostrix Polio) compared with Sanofi Pasteur MSD’s dTpa-IPV vaccine (Repevax), when co-administered with GSK Biologicals’ MMR vaccine (Priorix) in 3 and 4-year-old healthy children.
• Description: Thymidine is a pyrimidine nucleoside that is composed of the pyrimidine base thymine attached to the sugar deoxyribose. As a constituent of DNA, thymidine pairs with adenine in the DNA double helix. In cell biology it is used to synchronize the cells in G1/early S phase.
• Uses: Constituent of deoxyribonucleic acid Used for e.g. syntheses of zidovudine. Attributes For further information please contact us Contact Thymidine is used in the syntheses of active pharmaceutical ingredient such as zidovudine. It also pairs with deoxyadenosine in double-stranded deoxyribonucleic acid. It is used to synchronize the cells in G1/early S phase in cell biology.

Technology Process of Thymidine

There total 350 articles about Thymidine 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:

thymidine 3'(4-nitrophenylphosphate) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With sodium acetate buffer; PDMase; at 37 ℃; for 0.166667h; Rate constant;

DOI:10.1246/bcsj.56.549

Reference yield:

5'-d(AGTAT[5-ethynyl-U]GACCTA)-3' → 2'-deoxycytidine (959326-89-7) + 2'-Deoxyguanosine (961-07-9) + 2'-deoxy-5-ethynyluridine (61135-33-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

With tris hydrochloride; alkaline phosphatase; snake venom phosphodiesterase; at 37 ℃; pH=8.3; Enzymatic reaction;

DOI:10.1002/chem.201001572

Reference yield:

C23H39N4O7P → C19H25N3O12P(1-) + thymidine 5'-phosphate (365-07-1,15108-71-1,60363-32-8,96744-88-6,132696-16-3,143838-77-1) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrazole / acetonitrile / 4 h / 20 °C / Inert atmosphere

2: water; iodine / tetrahydrofuran; acetonitrile / 20 °C

3: hydrazinium monoacetate / methanol; dichloromethane / 2.5 h

4: water; sodium chloride / 72 h / 37 °C / pH 7.5 / Sealed tube; HEPES buffer; Enzymatic reaction

With tetrazole; water; iodine; hydrazinium monoacetate; sodium chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.3390/molecules16010552

upstream raw materials:

3',5'-di-O-toluoylthymidine

5-methyldeoxycytidine

5-bromo-2'-deoxyuridine

2'-deoxy-5-(hydroxymethyl)uridine

Downstream raw materials:

2'-deoxy-D-adenosine

2-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methyl-1,2,4-triazine-3,5(2H,4H)-dione

thymidine 3'-monophosphate

Thymidine 3',5'-diphosphate

Refernces

• 1、 Smiley-Moreno, Elizabeth,Smith, Douglas,Yu, Jieh-Juen,Cao, Phuong,Arulanandam, Bernard P.,Chambers, James P.. "Biochemical characterization of a recombinant acid phosphatase from Acinetobacter baumannii". . . Retrieved 2021/06/09.
• 2、 Bizzarri, Bruno Mattia,Fanelli, Angelica,Kapralov, Michail,Krasavin, Eugene,Saladino, Raffaele. "Meteorite-catalyzed intermoleculartrans-glycosylation produces nucleosides under proton beam irradiation". . p. 19258 - 19264. Retrieved 2021/06/03.