5-Propenyl deoxyuridine

Base Information

• Chemical Name: 5-Propenyl deoxyuridine
• CAS No.: 82768-44-3
• Molecular Formula: C₁₁H₁₃BrN₂O₅
• Molecular Weight: 333.139
• DSSTox Substance ID: DTXSID50860898
• Mol file: 82768-44-3.mol

Synonyms:5-propenyl deoxyuridine;SCHEMBL7601228;DTXSID50860898

Chemical Property of 5-Propenyl deoxyuridine

Chemical Property:

• PSA: 104.55000
• LogP: -0.45710
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 268.10592162
• Heavy Atom Count: 19
• Complexity: 445

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
• Isomeric SMILES: CC=CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O

Technology Process of 5-Propenyl deoxyuridine

There total 3 articles about 5-Propenyl 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: 69.0%

5-carboxyvinyl-2'-deoxyuridine (95119-96-3) → 5-bromovinyldeoxyuridine (82768-44-3)

Guidance literature:

With N-Bromosuccinimide; potassium acetate; In water;

DOI:10.1039/c4ra09798j

Reference yield:

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 5-bromovinyldeoxyuridine (82768-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium diacetate; triethylamine / water / 0.5 h / 80 °C / Irradiation

2: sodium hydroxide; hydrogenchloride

3: N-Bromosuccinimide; potassium acetate / water

With hydrogenchloride; N-Bromosuccinimide; potassium acetate; palladium diacetate; triethylamine; sodium hydroxide; In water; 1: |Heck Reaction;

DOI:10.1039/c4ra09798j

Reference yield:

5-(2-carbomethoxyvinyl)-2'-deoxyuridine (96244-97-2) → 5-bromovinyldeoxyuridine (82768-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; water

2: N-Bromosuccinimide

With N-Bromosuccinimide; water; sodium hydroxide;

DOI:10.1039/d0nj02803g

upstream raw materials:

5-Iodo-2'-deoxyuridine

5-carboxyvinyl-2'-deoxyuridine

5-(2-carbomethoxyvinyl)-2'-deoxyuridine

Refernces

• 1、 Ardhapure, Ajaykumar V.,Bag, Subhendu Sekhar,Bhilare, Shatrughn,Gayakhe, Vijay,Gunturu, Krishna Chaitanya,Kapdi, Anant R.,Sanghvi, Yogesh S.. "Extended fluorescent uridine analogues: synthesis, photophysical properties and selective interaction with BSA protein". . p. 14744 - 14754. Retrieved 2020/09/21.