5-Carboxy-2'-deoxyuridine

Base Information

• Chemical Name: 5-Carboxy-2'-deoxyuridine
• CAS No.: 14599-46-3
• Molecular Formula: C10H12 N2 O7
• Molecular Weight: 272.2115
• Hs Code.: 2934990002
• UNII: TP4HBV9HED
• Nikkaji Number: J767.987D
• Wikidata: Q27179272
• Mol file: 14599-46-3.mol

Synonyms:2'-deoxy-5-carboxyuridine;5-carboxy-2'-deoxyuridine

Chemical Property of 5-Carboxy-2'-deoxyuridine

Chemical Property:

• Melting Point: >144°C (dec.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 141.85000
• Density: 1.711g/cm³
• LogP: -2.12450
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 272.06445073
• Heavy Atom Count: 19
• Complexity: 461

Purity/Quality:

97% ^*data from raw suppliers

5-Carboxy-2''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C(=O)O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)C(=O)O)CO)O
• Uses: 5-Carboxy-2'-deoxyuridine, is a derivative of Trifluridine, an anti-herpesvirus antiviral drug, used primarily on the eye. 5-Carboxy-2''-deoxyuridine, is a derivative of Trifluridine, an anti-herpesvirus antiviral drug, used primarily on the eye.

Technology Process of 5-Carboxy-2'-deoxyuridine

There total 5 articles about 5-Carboxy-2'-deoxyuridine 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: 100.0%

5-ethoxycarbonyl-2'-deoxyuridine (180728-31-8) → 5-carboxy-2'-deoxyuridine (14599-46-3)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 16h;

DOI:10.1021/jo960614f

Reference yield: 90.0%

2'-deoxy-5-trifluoromethyluridine (70-00-8) → 5-carboxy-2'-deoxyuridine (14599-46-3)

Guidance literature:

With sodium hydroxide; at 37 ℃; for 36h; pH=10;

DOI:10.1081/NCN-120022739

Reference yield: 40.0%

1,3,4-tri-O-acetyl-2-deoxy-β-D-erythro-pentopyranose (4594-52-9,96291-74-6,96291-75-7) + 2,4-dihydroxypyrimidine-5-carboxylic acid (23945-44-0,76821-79-9) → 5-carboxy-2'-deoxyuridine (14599-46-3)

Guidance literature:

2,4-dihydroxypyrimidine-5-carboxylic acid; With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at 80 ℃; for 4h;

1,3,4-tri-O-acetyl-2-deoxy-β-D-erythro-pentopyranose; With tin(IV) chloride; In dichloromethane; at 20 ℃; for 5h;

DOI:10.3390/molecules22040672

upstream raw materials:

5-ethoxycarbonyl-2'-deoxyuridine

thymidine

2'-deoxy-5-trifluoromethyluridine

1,3,4-tri-O-acetyl-2-deoxy-β-D-erythro-pentopyranose

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-5-carboxyethyl-2'-deoxyuridine

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