5-Ethynyluridine

Base Information

• Chemical Name: 5-Ethynyluridine
• CAS No.: 69075-42-9
• Molecular Formula: C11H12N2O6
• Molecular Weight: 268.226
• Hs Code.: 29335990
• UNII: AV26TNA26B
• ChEMBL ID: CHEMBL3963835
• Nikkaji Number: J2.652.412A
• Mol file: 69075-42-9.mol

Synonyms:5-Ethynyluridine;69075-42-9;Uridine, 5-ethynyl-;5-ethynyl uridine;AV26TNA26B;1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-ethynylpyrimidine-2,4(1H,3H)-dione;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethynylpyrimidine-2,4-dione;1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-ethynylpyrimidine-2,4-(1H,3H)-dione;5-Ethynyl Uridine (EU);5-EU;5-Ethynyluridine?;UNII-AV26TNA26B;5-Ethynyluridine (5-EU);SCHEMBL3673387;CHEMBL3963835;QCWBIPKYTBFWHH-FDDDBJFASA-N;GLXC-25273;EX-A3665;MFCD00876719;AKOS024462949;DS-8002;AC-32359;PD150671;HY-141140;CS-0116049;C76184;A855702;J-700351;1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-ethynylpy

Chemical Property of 5-Ethynyluridine

Chemical Property:

• PKA: 8.29±0.10(Predicted)
• PSA: 124.78000
• Density: 1.67±0.1 g/cm3(Predicted)
• LogP: -2.87060
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated, Sonicated)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 268.06953611
• Heavy Atom Count: 19
• Complexity: 493

Purity/Quality:

98%min ^*data from raw suppliers

5-Ethynyluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C#CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Description: 5-Ethynyl uridine (5-EU) is an alkyne-containing metabolic labeling reagent used to detect global RNA transcription temporally and spatially in both in-vitro and in-vivo with the modified nucleotide. The alkyne handler can be used for subsequent ligation to azide-containing molecules through a highly efficient click chemistry reaction.
• Uses: 5-Ethynyluridine is used to help detect RNA synthesis in cells by its biosynthetic incorporation into newly transcribed RNA. This alkyne-bearing metabolic labeling reagent can be used to measure RNA synthesis in proliferating cells. Once fed to cells, this nucleoside is incorporated during active RNA synthesis and can then be detected using a copper-catalyzed click reaction with fluorescent dyes. The cells can then be analysed by fluorescence imaging, flow cytometry or high content imaging analysis.

Technology Process of 5-Ethynyluridine

There total 11 articles about 5-Ethynyluridine 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: 76.0%

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-((trimethylsilyl)ethynyl)pyrimidine-2,4(1H,3H)-dione → 5-ethynyluridine (69075-42-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2018.09.040

Reference yield: 49.0%

→ 5-ethynyluridine (69075-42-9)

Guidance literature:

Reference yield:

5-iodouridine (1024-99-3) → 5-ethynyluridine (69075-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / N,N-dimethyl-formamide / 6 h / 25 °C / Inert atmosphere

2: sodium methylate / methanol / 8 h / 25 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmc.2016.09.008

upstream raw materials:

Tri-O-acetyluridine

2',3',5'-tri-O-acetyl-5-iodouridine

2′,3′,5′-tri-O-acetyl-5-(ethynyl(2-trimethylsilyl))-uridine

2′,3′,5′-tri-O-acetyl-5-ethynyluridine

Downstream raw materials:

uridine

2-fluoroadenosine

5-ethynyluracil

α-D-ribofuranosyl-1-phosphate

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