1-(2-Deoxypentofuranosyl)-4,5-dihydroxypyrimidin-2(1H)-one

Base Information

• Chemical Name: 1-(2-Deoxypentofuranosyl)-4,5-dihydroxypyrimidin-2(1H)-one
• CAS No.: 5168-36-5
• Molecular Formula: C₉H₁₂N₂O₆
• Molecular Weight: 244.204
• NSC Number: 82265
• DSSTox Substance ID: DTXSID50965958
• Mol file: 5168-36-5.mol

Synonyms:5-OHdU;NSC82265;NCIOpen2_004274;SCHEMBL530166;SCHEMBL24420635;DTXSID50965958;NSC-82265;PD157354;FT-0772593;1-(2-Deoxypentofuranosyl)-4,5-dihydroxypyrimidin-2(1H)-one

Chemical Property of 1-(2-Deoxypentofuranosyl)-4,5-dihydroxypyrimidin-2(1H)-one

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 124.78000
• Density: 1.698g/cm³
• LogP: -2.11710
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly, Heated, Sonicated), Water (Slightly)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 244.06953611
• Heavy Atom Count: 17
• Complexity: 382

Purity/Quality:

99% ^*data from raw suppliers

2’-Deoxy-5-hydroxyuridine ^*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)O)CO)O
• Uses: 2’-Deoxy-5-hydroxyuridine is involved in the base excision repair (BER) mechanism in mitochondria.

Technology Process of 1-(2-Deoxypentofuranosyl)-4,5-dihydroxypyrimidin-2(1H)-one

There total 7 articles about 1-(2-Deoxypentofuranosyl)-4,5-dihydroxypyrimidin-2(1H)-one 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: 87.0%

2'-deoxyuridine (951-78-0,63844-76-8) → 5-hydroxy-2'-deoxyuridine (5168-36-5,13011-49-9)

Guidance literature:

2'-deoxyuridine; With bromine; In water;

With pyridine; water;

DOI:10.1021/tx970186o

Reference yield:

5-bromo-2'-deoxyuridine (59-14-3,723-73-9) → 5-hydroxy-2'-deoxyuridine (5168-36-5,13011-49-9)

Guidance literature:

With lead dioxide;

DOI:10.1021/ja01608a053

Reference yield:

2'-Deoxycytidine (951-77-9) → 5-hydroxy-2'-deoxyuridine (5168-36-5,13011-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaNO₂; aqueous acetic acid

2: bromine

3: PbO₂

With bromine; lead dioxide; acetic acid; sodium nitrite;

DOI:10.1021/ja01608a053

upstream raw materials:

5-bromo-2'-deoxyuridine

2'-deoxyuridine

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

uridine

Downstream raw materials:

5-(Trifluoromethanesulfonyloxy)-2'-deoxyuridine

5-<(cyanomethylene)oxy>-2'-deoxyuridine

3-(cyanomethyl)-5-hydroxy-2'-deoxyuridine

3-(cyanomethyl)-5-<(cyanomethylene)oxy>-2'-deoxyuridine