5-Fluoro-6-iodouridine

Base Information

• Chemical Name: 5-Fluoro-6-iodouridine
• CAS No.: 87818-06-2
• Molecular Formula: C9H10FIN2O6
• Molecular Weight: 388.091
• ChEMBL ID: CHEMBL464221
• DSSTox Substance ID: DTXSID90583099
• Wikidata: Q72473767
• Mol file: 87818-06-2.mol

Synonyms:5-Fluoro-6-iodouridine;87818-06-2;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-6-iodopyrimidine-2,4-dione;CHEMBL464221;SCHEMBL1363655;DTXSID90583099;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-6-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

Chemical Property of 5-Fluoro-6-iodouridine

Chemical Property:

• PSA: 125.04000
• Density: 2.31 g/cm³
• LogP: -1.69590
• Storage Temp.: 2-8°C
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 387.95676
• Heavy Atom Count: 19
• Complexity: 458

Purity/Quality:

97% ^*data from raw suppliers

5-Fluoro-6-iodouridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(O1)N2C(=C(C(=O)NC2=O)F)I)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@H]([C@@H](O1)N2C(=C(C(=O)NC2=O)F)I)O)O)O

Technology Process of 5-Fluoro-6-iodouridine

There total 5 articles about 5-Fluoro-6-iodouridine 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: 90.0%

5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylidene-5-fluoro-6-iodouridine (1134188-90-1) → 5-fluoro-6-iodouridine (87818-06-2)

Guidance literature:

With trifluoroacetic acid; In water; at 0 - 20 ℃; Darkness;

DOI:10.1021/jm801224t

Reference yield: 86.0%

5-Fluoro-6-iodo-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione (87818-01-7) → 5-fluoro-6-iodouridine (87818-06-2)

Guidance literature:

With trifluoroacetic acid; Ambient temperature;

DOI:10.1248/cpb.31.2164

Reference yield:

5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione (87817-91-2) → 5-fluoro-6-iodouridine (87818-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / LDA, iodine / tetrahydrofuran / -70 °C

2: 86 percent / 50percent aqueous CF₃COOH / Ambient temperature

With iodine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1248/cpb.31.2164

upstream raw materials:

5-Fluoro-6-iodo-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

5-Fluoro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

2',3'-O-isopropylidene-5-fluorouridine

5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylidene-5-fluoro-6-iodouridine