5-Iodo-2'-deoxycytidine

Base Information

• Chemical Name: 5-Iodo-2'-deoxycytidine
• CAS No.: 611-53-0
• Molecular Formula: C9H12IN3O4
• Molecular Weight: 353.116
• Hs Code.: 29071212
• European Community (EC) Number: 210-269-8
• UNII: 3EK8532DZV
• DSSTox Substance ID: DTXSID50209985
• Nikkaji Number: J252.498H
• Wikipedia: Ibacitabine
• Wikidata: Q5983577
• NCI Thesaurus Code: C83771
• Metabolomics Workbench ID: 154556
• ChEMBL ID: CHEMBL2104340
• Mol file: 611-53-0.mol

Synonyms:2'-deoxy-5-iodocytidine;5-iodo-2'-deoxycytidine;5-iodo-2'-deoxycytidine, 125I-labeled;5-iododeoxycytidine;ibacitabine;iododeoxycytidine

Chemical Property of 5-Iodo-2'-deoxycytidine

Chemical Property:

• Melting Point: 180-183℃
• Boiling Point: 522.1 °C at 760 mmHg
• PKA: 14.03±0.60(Predicted)
• Flash Point: 269.6 °C
• PSA: 110.60000
• Density: 2.37 g/cm³
• LogP: -0.34800
• Storage Temp.: Store at 0°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 352.98725
• Heavy Atom Count: 17
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

2''-Deoxy-5-iodocytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 22-63-42/43-36/37/38
• Safety Statements: 23-26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)I)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)I)CO)O
• Description: 5-Iodo-2'-deoxycytidine is an iodinated analog of deoxycytidine and acts as an anti-viral agent.
• Uses: 5-Iodo-2'-deoxycytidine is used in the construction of DNA oligomers to enable structural studies and photoactivated cross-linking. It is used in the synthesis of other modified nucleosides, such as 5-ethynylferrocenyl-2?-deoxycytidine used in semiconductor electrodes and 10-(2-deoxyβ-D-ribofuranosyl)pyrimido[4?,5?:4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dCPPI).

Technology Process of 5-Iodo-2'-deoxycytidine

There total 4 articles about 5-Iodo-2'-deoxycytidine 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: 71.0%

2'-Deoxycytidine (951-77-9) → 5-Iodo-2'-deoxycytidine (611-53-0)

Guidance literature:

With iodine; 3-chloro-benzenecarboperoxoic acid; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.orglett.9b03801

Reference yield: 62.0%

→ 5-Iodo-2'-deoxycytidine (611-53-0)

Guidance literature:

Reference yield:

2'-deoxycytidine monohydrate (207121-53-7,652157-52-3) → 5-Iodo-2'-deoxycytidine (611-53-0)

Guidance literature:

With iodine; mercury(II) diacetate; In methanol; dichloromethane;

upstream raw materials:

2'-deoxycytidine monohydrate

2'-Deoxycytidine

2'-deoxycytidine monohydrochloride

Downstream raw materials:

N-{3-[4-Amino-1-((4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide

4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-(prop-1-ynyl)pyrimidin-2H-2-one

5-(4-benzoylthio-1-butynyl)-2'-deoxycytidine

1-[2-deoxy-5-O-(4,4′-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-iodocytosine

Refernces

• 1、 Romero-Pérez, Sonia,López-Martín, Isabel,Martos-Maldonado, Manuel C.,Somoza, álvaro,González-Rodríguez, David. "Synthesis of Phosphoramidite Monomers Equipped with Complementary Bases for Solid-Phase DNA Oligomerization". supporting information. p. 41 - 45. Retrieved 2020/01/03.
• 2、 -. "NUCLEIC ACIDSBUILDING BLOCKS AND METHODS FOR THE SYNTHESIS OF 5-HYDROXYMETHYLCYTOSINE-CONTAINING". Page/Page column 13; 14. . Retrieved 2012/05/31.