Ropidoxuridine

Base Information

• Chemical Name: Ropidoxuridine
• CAS No.: 93265-81-7
• Molecular Formula: C9H11IN2O4
• Molecular Weight: 338.102
• UNII: 3HX21A3SQF
• DSSTox Substance ID: DTXSID00239353
• Nikkaji Number: J370.002J
• Wikidata: Q27257237
• NCI Thesaurus Code: C48813
• Metabolomics Workbench ID: 149804
• ChEMBL ID: CHEMBL2103821
• Mol file: 93265-81-7.mol

Synonyms:1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone;5-iodo-2-pyrimidinone 2' deoxyribonucleoside;5-iodo-2-pyrimidinone-2'-deoxyribose;IPdR;ropidoxuridine

Chemical Property of Ropidoxuridine

Chemical Property:

• Boiling Point: 478.6 °C at 760 mmHg
• Flash Point: 243.3 °C
• PSA: 84.58000
• Density: 2.22 g/cm³
• LogP: -0.51140
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 337.97635
• Heavy Atom Count: 16
• Complexity: 357

Purity/Quality:

99% ^*data from raw suppliers

ROPIDOXURIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C=NC2=O)I)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C=NC2=O)I)CO)O
• Recent ClinicalTrials: Ropidoxuridine in Treating Patients With Advanced Gastrointestinal Cancer Undergoing Radiation Therapy
• Uses: Ropidoxuridine is a pyrimidinone nucleoside prodrug of 5-iododeoxyuridine (IUdR) (I205750), an antitumor nucleoside enantiomer thymidine kinase used as potential antiviral agents.

Technology Process of Ropidoxuridine

There total 3 articles about Ropidoxuridine 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: 53.0%

1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl>-5-iodo-2-pyrimidinone (96245-84-0) → 1-(2-Deoxy-beta-D-ribofuranosyl)-5-(iodo)-2-pyrimidinone (93265-81-7)

Guidance literature:

With ammonia; In methanol; at -15 - 12 ℃; for 15h; Temperature; Inert atmosphere;

Reference yield: 41.7%

(2R,3S,5R)-5-(5-iodo-2-oxopyrimidin-1(2H)-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate → 1-(2-Deoxy-beta-D-ribofuranosyl)-5-(iodo)-2-pyrimidinone (93265-81-7)

Guidance literature:

With ammonia; In methanol; for 24h; Cooling with ice; Sealed tube;

Reference yield:

→ 1-(2-Deoxy-beta-D-ribofuranosyl)-5-(iodo)-2-pyrimidinone (93265-81-7)

Guidance literature:

upstream raw materials:

1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl>-5-iodo-2-pyrimidinone

Downstream raw materials:

C₁₃H₁₇IN₄O₈

Refernces

• 1、 -. "IDOXURIDINE AND ITS ANALOGS AS NEUROPROTECTANS FOR THE TREATMENT OF PARKINSONISM". Page/Page column 22; 27; 28. . Retrieved 2018/08/26.
• 2、 -. "NOVEL 5-SUBSTITUTED 2-PYRIMIDINONE NUCLEOSIDES AND METHODS OF USE". . . Retrieved 2008/06/13.