5-(2-Carboxyethenyl)uridine

Base Information

• Chemical Name: 5-(2-Carboxyethenyl)uridine
• CAS No.: 99394-52-2
• Molecular Formula: C₁₂H₁₄N₂O₈
• Molecular Weight: 314.252
• DSSTox Substance ID: DTXSID40706711
• Mol file: 99394-52-2.mol

Synonyms:5-(2-Carboxyethenyl)uridine;DTXSID40706711

Chemical Property of 5-(2-Carboxyethenyl)uridine

Chemical Property:

• PSA: 162.08000
• LogP: -2.75410
• XLogP3: -2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 314.07501541
• Heavy Atom Count: 22
• Complexity: 557

Purity/Quality:

98%Min ^*data from raw suppliers

(E)-5-(2-Carboxyvinyl)uridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)C=CC(=O)O
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C=CC(=O)O
• Uses: (E)-5-(2-Carboxyvinyl)uridine can be used in sulfur-?containing uridine anti-?cancer compound (4-?thioxo-?5-?(2-?halovinyl)?uridine)?, and its intermediate, preparation method and application.

Technology Process of 5-(2-Carboxyethenyl)uridine

There total 4 articles about 5-(2-Carboxyethenyl)uridine 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: 99.0%

(E)-5-<2-(ethoxycarbonyl)vinyl>uridine (123881-85-6) → (E)-5-(2-carboxyvinyl)uridine (99394-52-2)

Guidance literature:

With potassium hydroxide; at 25 ℃; for 2h;

DOI:10.1021/jm00164a039

Reference yield: 92.34%

methyl 3-(5-uridinyl)propenoate (58931-19-4) → (E)-5-(2-carboxyvinyl)uridine (99394-52-2)

Guidance literature:

With water; sodium hydroxide; at 20 ℃; for 3h;

Reference yield:

5-iodouridine (1024-99-3) → (E)-5-(2-carboxyvinyl)uridine (99394-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Pd(OAc)2, Ph₃P, TEA / 1 h / Heating

2: 67 percent / aq. 1 N NaOH / Ambient temperature

With palladium diacetate; sodium hydroxide; TEA; triphenylphosphine;

DOI:10.1021/jm00152a008

upstream raw materials:

(E)-5-<2-(ethoxycarbonyl)vinyl>uridine

methyl 3-(5-uridinyl)propenoate

5-iodouridine

uridine

Downstream raw materials:

5-(1-methoxy-2-iodoethyl)uridine

5-(1-hydroxy-2-iodoethyl)uridine

(E)-5-(2-bromovinyl)uridine

5-(1,2-dibromo-2-succinimidoethyl)uridine

Refernces

• 1、 Kumar, Rakesh,Xu, Lihua,Knaus, Edward E.,Wiebe, Leonard I.,Tovell, Dorothy R.,et al.. "Synthesis and Antiviral and Cytotoxic Activity of Iodohydrin and Iodomethoxy Derivatives of 5-Vinyl-2'-deoxyuridines, 2'-Fluoro-2'-deoxyuridine, and Uridine". . p. 717 - 723. Retrieved 2007/10/02.