(E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE

Base Information

• Chemical Name: (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE
• CAS No.: 74131-06-9
• Molecular Formula: C12H14 N2 O7
• Molecular Weight: 298.252
• Mol file: 74131-06-9.mol

Synonyms:(E)-5-(2-CARBOXYVINYL)-2’-DEOXYURIDINE

Chemical Property of (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE

Chemical Property:

• Melting Point: 272.22 (Mean or Weighted MP)
• Boiling Point: (deg C): 627.63 (Adapted Stein & Brown method)
• PKA: 4.20±0.10(Predicted)
• PSA: 141.85000
• Density: 1.682 g/cm3
• LogP: -1.72490
• Solubility.: DMSO; Pyridine

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (E)-5-(2-Carboxyvinyl)-2’-deoxyuridine are used for reversible photoligation. It can also be used for genomic research, biotechnology, and biomedical agents.

Technology Process of (E)-5-(2-CARBOXYVINYL)-2'-DEOXYURIDINE

There total 7 articles about (E)-5-(2-CARBOXYVINYL)-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: 90.0%

methyl (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate (86163-17-9) → (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)

Guidance literature:

methyl (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate; With sodium hydroxide; for 3h;

With hydrogenchloride; In water; at 4 ℃; pH=2;

DOI:10.1039/c5ra01461a

Reference yield: 68.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 2-[2-[N,N-bis(2-trifluoroacetamidoethyl)]-aminoethyl]carbamoyl-(E)-vinyl)-2'-deoxyuridine + (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)

Guidance literature:

With hydrogenchloride; sodium hydroxide; triethylamine; triphenylphosphine; palladium diacetate; In 1,4-dioxane; water;

Reference yield: 66.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + ethyl acrylate (140-88-5,9003-32-1) → (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)

Guidance literature:

With Amberlite IRA-67; palladium on activated charcoal; In N,N-dimethyl-formamide; at 50 ℃; for 6h;

DOI:10.1039/b505737j

upstream raw materials:

methyl (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate

5-Iodo-2'-deoxyuridine

ethyl acrylate

acrylic acid methyl ester

Downstream raw materials:

5-vinyl-2'-deoxyuridine

5-(1,2-dibromo-2-succinimidoethyl)-2'-deoxyuridine

(E)-5-(2-bromovinyl)-2'-deoxyuridine

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