5-Formyl-2'-deoxyuridine

Base Information

• Chemical Name: 5-Formyl-2'-deoxyuridine
• CAS No.: 4494-26-2
• Molecular Formula: C10H12 N2 O6
• Molecular Weight: 256.215
• Nikkaji Number: J70.312E
• ChEMBL ID: CHEMBL379296
• Mol file: 4494-26-2.mol

Synonyms:2'-deoxy-5-formyluridine;5-FdU;5-formyl-2'-deoxyuridine;5-formyldeoxyuridine

Chemical Property of 5-Formyl-2'-deoxyuridine

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 8.23±0.10(Predicted)
• Flash Point: °C
• PSA: 121.62000
• Density: 1.67g/cm³
• LogP: -2.01020
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly, Sonicated)
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 256.06953611
• Heavy Atom Count: 18
• Complexity: 421

Purity/Quality:

99%, ^*data from raw suppliers

1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C=O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)C=O)CO)O

Technology Process of 5-Formyl-2'-deoxyuridine

There total 28 articles about 5-Formyl-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: 98.0%

5-1,N3-di-(3,5-dichlorophenyl)-imidazolidino-2->-2'-deoxyuridine (163593-10-0) → 5-formyl-2'-deoxyuridine (4494-26-2)

Guidance literature:

With acetic acid; at 50 ℃; for 16h;

DOI:10.1248/cpb.42.2231

Reference yield: 93.0%

3',5'-di-O-acetyl-2'-deoxy-5-formyluridine (86163-30-6) → 5-formyl-2'-deoxyuridine (4494-26-2)

Guidance literature:

With triethylamine; In methanol; water; at 20 ℃; for 2h;

DOI:10.1007/s11171-005-0076-7

Reference yield: 88.0%

3',5'-bis-O-(tert-butyldimethylsilyl)-5-(formyl)-2'-deoxyuridine (142667-68-3) → 5-formyl-2'-deoxyuridine (4494-26-2)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In ethyl acetate; at 20 ℃; for 62h;

DOI:10.1021/ja403229y

upstream raw materials:

thymidine

5-1,N³-di-(3,5-dichlorophenyl)-imidazolidino-2->-2'-deoxyuridine

2'-deoxy-5-(1,2-dihydroxyethyl)uridine

5-(N-methoxymethylamine)-2'-deoxyuridine

Downstream raw materials:

bis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)[1-(2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]methane

2-amino-4-[1-(2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-4,5-dihydro-7-methyl-5-oxo-pyrano[4,3-b]pyran-3-carbonitrile

bis(1,2-dihydro-4-hydroxy-6-methyl-2-oxopyridin-3-yl)[1-(2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]methane

2-amino-4-[1-(2-deoxy-β-D-ribosyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-5,6-dihydro-7-methyl-5-oxo-4H-pyrano[3,2-c]pyridine-3-carbonitrile

Refernces

• 1、 Bali Mehta, Shilpika,Kumar, Banty,Kumar, Sandeep,Kumar, Sumit,Maity, Jyotirmoy,Prasad, Ashok K.. "Synthesis and photophysical properties of 5-(3′′-alkyl/aryl-amino-1′′-azaindolizin-2′′-yl)-2′-deoxyuridines". . p. 16635 - 16647. Retrieved 2021/09/27.
• 2、 Zhou, Qian,Li, Kun,Liu, Yan-Hong,Li, Ling-Ling,Yu, Kang-Kang,Zhang, Hong,Yu, Xiao-Qi. "Fluorescent Wittig reagent as a novel ratiometric probe for the quantification of 5-formyluracil and its application in cell imaging". . p. 13722 - 13725. Retrieved 2019/01/03.