5-Vinyl-2'-deoxyuridine

Base Information

• Chemical Name: 5-Vinyl-2'-deoxyuridine
• CAS No.: 55520-67-7
• Molecular Formula: C11H14 N2 O5
• Molecular Weight: 254.243
• UNII: 87V72AT994
• DSSTox Substance ID: DTXSID10970866
• Nikkaji Number: J59.525J
• Wikidata: Q27269846
• ChEMBL ID: CHEMBL221928
• Mol file: 55520-67-7.mol

Synonyms:2'-deoxy-5-vinyluridine;5-vinyl-2'-deoxyuridine

Chemical Property of 5-Vinyl-2'-deoxyuridine

Chemical Property:

• Refractive Index: 1.5700 (estimate)
• Boiling Point: 397.45°C (rough estimate)
• PSA: 104.81000
• Density: 1.2983 (rough estimate)
• LogP: -0.76740
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 254.09027155
• Heavy Atom Count: 18
• Complexity: 420

Purity/Quality:

99% ^*data from raw suppliers

5-VINYL-2'-DEOXYURIDINE 95.00% ^*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)C2CC(C(O2)CO)O
• Isomeric SMILES: C=CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O

Technology Process of 5-Vinyl-2'-deoxyuridine

There total 22 articles about 5-Vinyl-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: 92.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + tri-n-butyl(vinyl)tin (7486-35-3) → 5-vinyl-2'-deoxyuridine (55520-67-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 12h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2014.12.100

Reference yield: 58.0%

(E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid (74131-06-9) → 5-vinyl-2'-deoxyuridine (55520-67-7)

Guidance literature:

With water; triethylamine; In N,N-dimethyl-formamide; at 105 ℃; for 24h;

DOI:10.1039/P19870000457

Reference yield: 56.0%

vinyl acetate (108-05-4,9003-20-7) + 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 5-vinyl-2'-deoxyuridine (55520-67-7)

Guidance literature:

With tributyl-amine; palladium diacetate; In N,N-dimethyl-formamide; at 80 ℃; for 0.333333h; Microwave irradiation;

DOI:10.1039/b904941j

upstream raw materials:

5-Iodo-2'-deoxyuridine

tri-n-butyl(vinyl)tin

2'-deoxy-5-(1-phenylthioethyl)uridine

2'-deoxy-5-(1-phenylsulphinylethyl)uridine

Downstream raw materials:

2'-deoxy-5-(2-phenylthioethyl)uridine

2'-deoxy-5-(1-phenylthioethyl)uridine

3',5'-bis-(O-tert-butyldimethylsilyl)-5-vinyl-2'-deoxyuridine

5-((E)-2-chlorovinyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-pyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 Kore, Anilkumar R.,Yang, Bo,Srinivasan, Balasubramanian. "Synthesis of 5-[3,6-di(pyridin-2-yl)pyridazine-4-yl]-2′-deoxyuridine-5′-O-triphosphate - A potential probe for fluorescence detection and imaging DNA". . p. 808 - 811. Retrieved 2015.
• 2、 -. "PHOTORESPONSIVE NUCLEIC ACID MANUFACTURING METHOD". Page/Page column 20-21. . Retrieved 2010/12/17.