3',5'-Di-O-acetyl-5-chloro-2'-deoxyuridine

Base Information

• Chemical Name: 3',5'-Di-O-acetyl-5-chloro-2'-deoxyuridine
• CAS No.: 6046-63-5
• Molecular Formula: C₁₃H₁₅ClN₂O₇
• Molecular Weight: 346.724
• DSSTox Substance ID: DTXSID10451483
• Nikkaji Number: J331.851F
• Wikidata: Q82271533
• Mol file: 6046-63-5.mol

Synonyms:6046-63-5;3',5'-Di-O-acetyl-5-chloro-2'-deoxyuridine;5-Chloro-3',5'-di-O-acetyl-2'-deoxyuridine;[(2R,3S,5R)-3-Acetyloxy-5-(5-chloro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate;DTXSID10451483;2'-Deoxy-3'-O,5'-O-diacetyl-5-chlorouridine;3/',5/'-Di-O-acetyl-5-chloro-2/'-deoxyuridine

Chemical Property of 3',5'-Di-O-acetyl-5-chloro-2'-deoxyuridine

Chemical Property:

• Refractive Index: 1.565
• PSA: 157.15000
• Density: 1.49g/cm³
• LogP: 0.23530
• Solubility.: Ethyl Acetate
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 346.0567785
• Heavy Atom Count: 23
• Complexity: 577

Purity/Quality:

98%Min ^*data from raw suppliers

5-Chloro-3’,5’-di-O-acetyl-2''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(CC(O1)N2C=C(C(=O)NC2=O)Cl)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H](C[C@@H](O1)N2C=C(C(=O)NC2=O)Cl)OC(=O)C
• Uses: 5-Chloro-35di-O-acetyl-2'-deoxyuridine is a halogenated uridine derivative used in pharmaceutical compositions.

Technology Process of 3',5'-Di-O-acetyl-5-chloro-2'-deoxyuridine

There total 3 articles about 3',5'-Di-O-acetyl-5-chloro-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: 95.0%

3',5'-di-O-acetyl-2'-deoxyuridine (13030-62-1) → 1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-chlorouracil (6046-63-5)

Guidance literature:

With ammonium cerium(IV) nitrate; lithium chloride; In acetic acid; acetonitrile; at 80 ℃; for 6h;

DOI:10.1021/jo00303a033

Reference yield:

acetic anhydride (108-24-7) + 5-chloro-2'-deoxyuridine (50-90-8,188559-94-6) → 1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-chlorouracil (6046-63-5)

Guidance literature:

With pyridine; at 0 ℃; for 5h;

DOI:10.1002/mrc.3980

Reference yield:

→ 1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-chlorouracil (6046-63-5)

Guidance literature:

5-Chlor-2'-deoxy-uridin, Acetanhydrid;

upstream raw materials:

3',5'-di-O-acetyl-2'-deoxyuridine

acetic anhydride

5-chloro-2'-deoxyuridine

Downstream raw materials:

5-Chloro-5'-O-p-tolylsulphonyl-2'-deoxyuridine

5-chloro-2'-deoxyuridine

Refernces

• 1、 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.
• 2、 Kumar,Wiebe,Knaus. "A mild and efficient methodology for the synthesis of 5-halogeno uracil nucleosides that occurs via a 5-halogeno-6-azido-5,6-dihydro intermediate". . p. 2005 - 2010. Retrieved 2007/10/02.