2'-Deoxyuridine

Base Information

• Chemical Name: 2'-Deoxyuridine
• CAS No.: 951-78-0
• Molecular Formula: C9H12N2O5
• Molecular Weight: 228.205
• Hs Code.: 2933.59 DERIVATION
• NSC Number: 23615
• DSSTox Substance ID: DTXSID60862484
• Wikidata: Q105174155
• Mol file: 951-78-0.mol

Synonyms:1-(2-Deoxy-b-D-erythro-pentofuranosyl)uracil;2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-;2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-b-D-ribofuranosyl)-;2'-Desoxyuridine;Deoxyribose uracil;Deoxyuridine;NSC 23615;Uracildeoxyriboside;1-(2-Deoxy-b-D-ribofuranosyl)uracil;1-(2-Deoxy-D-erythro-pentofuranosyl)uracil;Uridine, 2'-deoxy-;

Chemical Property of 2'-Deoxyuridine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 167-169 °C(lit.)
• Refractive Index: 52 ° (C=1, 1mol/L NaOH)
• Boiling Point: 370.01°C (rough estimate)
• PKA: pKa 9.3(H2O t = 25) (Uncertain)
• PSA: 104.55000
• Density: 1.533 g/cm³
• LogP: -1.82270
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
• Water Solubility.: 300 g/L (20 ºC)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 228.07462149
• Heavy Atom Count: 16
• Complexity: 343

Purity/Quality:

≥99% ^*data from raw suppliers

2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC(=O)NC2=O)CO)O
• Description: 2'-Deoxyuridine is a natural deoxynucleoside, which can be directly used to prepare combined deoxynucleoside drugs or used as chemical reagents for biochemical research. At the same time, it can be used as an intermediate to synthesize some antiviral nucleoside drugs and molecular markers, such as 8-bromo-2-deoxyuridine and 8-hydroxy-2-deoxyuridine from 2'-Deoxyuridine. 2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. 2'-Deoxyuridine has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. 2'-Deoxyuridine is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.
• Physical properties: 2'-Deoxyuridine is a white or off-white powdered solid with a melting point of 167 to 169 °C. Its boiling point is roughly estimated to be 370.01°C. It is slightly soluble in water, DMSO, and slightly soluble in methanol when heated.
• Uses: 2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples. 2′-Deoxyuridine (dU) is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2′-Deoxyuridines used as labeling substrates include chloro-2′-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2′-deoxyuridine include 5-ethynyl-2′-deoxyuridine (DdU) and 5-hydroxymethyl-2′-deoxyuridine (HmdU). An uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease

Technology Process of 2'-Deoxyuridine

There total 97 articles about 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%

4-O-(2,4,6-Trimethylphenyl)-2'-deoxyuridine (130197-82-9) → 2'-deoxyuridine (951-78-0,63844-76-8) + 2'-Deoxycytidine (951-77-9)

Guidance literature:

With ammonium hydroxide; at 65 ℃; for 2h;

DOI:10.1016/S0040-4020(01)81793-2

Reference yield: 72.0%

3'-O-acetyl-5'-O-t-butyldimethylsilyl-2'-deoxyuridine (1140622-65-6) + benzyl alcohol (100-51-6,185532-71-2) → (benzyloxy)(tert-butyl)dimethylsilane (53172-91-1) + 2'-deoxyuridine (951-78-0,63844-76-8) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 3'-O-acetyl-2'-deoxyuridine (23197-88-8)

Guidance literature:

With copper(II) sulfate; In xylene; for 2h; Heating;

DOI:10.1080/15257770802257846

Reference yield: 49.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 2'-deoxyuridine (951-78-0,63844-76-8) + C5-(allyl)-2'-deoxyuridine (73-39-2)

Guidance literature:

With allyl-trimethyl-silane; In water; acetonitrile; Irradiation;

DOI:10.1016/S0040-4039(00)98361-8

upstream raw materials:

O^5'-acetyl-2'-iodo-2'-deoxy-uridine

2'-Deoxycytidine

1-(O³,O⁵-bis-trimethylsilanyl-β-D-erythro-2-deoxy-pentofuranosyl)-5-bromo-4-trimethylsilanyloxy-1H-pyrimidin-2-one

trimethylaluminum

Downstream raw materials:

2'-deoxy-5-(hydroxymethyl)uridine

Tetrahydrodeoxyuridine

5-bromo-2'-deoxyuridine

5-Iodo-2'-deoxyuridine

Refernces

• 1、 Peng, Haihui,Jie, Jialong,Mortimer, Ifor P.,Ma, Zehan,Su, Hongmei,Greenberg, Marc M.. "Reactivity and DNA Damage by Independently Generated 2′-Deoxycytidin-N4-yl Radical". . p. 14738 - 14747. Retrieved 2021/09/18.
• 2、 Mondal, Santanu,Mugesh, Govindasamy. "Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds". . p. 1773 - 1780. Retrieved 2019/01/10.