Uridine,5-chloro-2'-deoxy-

Base Information

• Chemical Name: Uridine,5-chloro-2'-deoxy-
• CAS No.: 50-90-8
• Molecular Formula: C9H11 Cl N2 O5
• Molecular Weight: 262.65
• Hs Code.: 2942000000
• European Community (EC) Number: 623-009-7
• Nikkaji Number: J816.061I
• ChEMBL ID: CHEMBL1256348
• Mol file: 50-90-8.mol

Synonyms:Uridine,5-chloro-2'-deoxy-;188559-94-6;5-chloro-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;50-90-8;5-Chloro-1-((2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;C9H11ClN2O5;C9-H11-Cl-N2-O5;CHEMBL1256348;SCHEMBL15623877;1-(2-Deoxy-beta-D-lyxofuranosyl)-5-chlorouracil;W-202912;1-(2-Deoxy-beta-D-threo-pentofuranosyl)-5-chlorouracil;5-chloro-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

Chemical Property of Uridine,5-chloro-2'-deoxy-

Chemical Property:

• Melting Point: 176-179°C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 7.73±0.10(Predicted)
• Flash Point: °C
• PSA: 104.55000
• Density: 1.67 g/cm³
• LogP: -1.16930
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 262.0356491
• Heavy Atom Count: 17
• Complexity: 386

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Chloro-2''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)Cl)CO)O
• Isomeric SMILES: C1[C@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)Cl)CO)O
• Description: 5-Chloro-2''-deoxyuridine (CldU) is a thymidine analog that is readily incorporated, following phosphorylation, into newly synthesized DNA in place of thymidine. Like 5-bromo-2’-deoxyuridine and 5-iodo-2’-deoxyuridine, CldU can be detected immunologically in cells and tissues. CldU can also be added to cells or tissues sequentially with another thymidine analog to label temporally distinct populations. The insertion of thymidine analogs, including CldU, can significantly alter DNA processing and replication, so these analogs have also been used as mutagens, clastogens, and antiviral compounds.
• Uses: A halogenated uridine derivative used in pharmaceutical compositions. 5-Chloro-2'-deoxyuridine (CldU) is a thymidine analog that is readily incorporated, following phosphorylation, into newly synthesized DNA in place of thymidine. Like 5-bromo-2’-deoxyuridine and 5-iodo-2’-deoxyuridine, CldU can be detected immunologically in cells and tissues. CldU can also be added to cells or tissues sequentially with another thymidine analog to label temporally distinct populations. The insertion of thymidine analogs, including CldU, can significantly alter DNA processing and replication, so these analogs have also been used as mutagens, clastogens, and antiviral compounds.[Cayman Chemical] 5-Chloro-2′-deoxyuridine (CldU) is used as a thymidine analog to study the miscoding potential of hypochlorous acid damage to DNA and DNA precursors. When used with antibody based immunofluorescent imaging, 5-Chloro-2′-deoxyuridine incorporation may be used in protocols to identify sites of DNA replication. CldU may be used as a labeling substrate in conjunction with other halogenated uridine labeling substrates such as iododeoxyuridine (IdU).

Technology Process of Uridine,5-chloro-2'-deoxy-

There total 8 articles about Uridine,5-chloro-2'-deoxy- 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: 94.8%

1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-chlorouracil (6046-63-5) → 5-chloro-2'-deoxyuridine (50-90-8,188559-94-6)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00303a033

Reference yield: 92.0%

2'-deoxyuridine (951-78-0,63844-76-8) → 5-chloro-2'-deoxyuridine (50-90-8,188559-94-6)

Guidance literature:

With N-chloro-succinimide; 1-ethylene glycol monomethyl ether-3-methylimidazolium methanesulfonate; at 50 ℃; for 20h;

DOI:10.1055/s-0029-1217042

Reference yield: 6.0%

5-chlorouracil (1820-81-1) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5-chloro-2'-deoxyuridine (50-90-8,188559-94-6)

Guidance literature:

With Lactobacillus animalis ATCC 35046 2’-N-deoxyribosyltransferase immobilized in DEAE-Sepharose; In aq. buffer; at 30 ℃; pH=7; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.jfluchem.2016.04.012

upstream raw materials:

2'-deoxyuridine

1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-chlorouracil

5-Iodo-2'-deoxyuridine

5-chlorouracil

Downstream raw materials:

5-chlorouracil

1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-chlorouracil

5-chloro-2’-deoxy-5’-O-dimethoxytrityluridine

4'-azido-5-chloro-2',5'-dideoxy-5'-iodo-3'-O-(4-methoxybenzoyl)uridine

Refernces

• 1、 Hatano, Akihiko,Wakana, Hiroyuki,Terado, Nanae,Kojima, Aoi,Nishioka, Chisato,Iizuka, Yu,Imaizumi, Takuya,Uehara, Sanae. "Bio-catalytic synthesis of unnatural nucleosides possessing a large functional group such as a fluorescent molecule by purine nucleoside phosphorylase". . p. 5122 - 5129. Retrieved 2019/10/05.
• 2、 Yueh, Han,Yu, Hongchuan,Theile, Christopher S.,Pal, Ayan,Horhota, Allen,Greco, Nicholas,Christianson, Carl V.,McLaughlin, Larry W.. "Synthesis and properties of DNA containing cyclonucleosides". . p. 661 - 679. Retrieved 2012/11/07.