5'-O-acetyl-3'-azido-2',3'-dideoxyuridine

Base Information

• Chemical Name: 5'-O-acetyl-3'-azido-2',3'-dideoxyuridine
• CAS No.: 84472-87-7
• Molecular Formula: C11H13 N5 O5
• Molecular Weight: 295.255
• Nikkaji Number: J3.382.586B
• Mol file: 84472-87-7.mol

Synonyms:NLHQFBSARLTXOR-QXFUBDJGSA-N;5'-O-acetyl-3'-azido-2',3'-dideoxyuridine

Chemical Property of 5'-O-acetyl-3'-azido-2',3'-dideoxyuridine

Chemical Property:

• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 295.09166853
• Heavy Atom Count: 21
• Complexity: 541

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(CC(O1)N2C=CC(=O)NC2=O)N=[N+]=[N-]
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H](C[C@@H](O1)N2C=CC(=O)NC2=O)N=[N+]=[N-]

Technology Process of 5'-O-acetyl-3'-azido-2',3'-dideoxyuridine

There total 8 articles about 5'-O-acetyl-3'-azido-2',3'-dideoxyuridine 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: 97.0%

5'-O-acetyl-3'-azido-3'-deoxy-3-[(E)-2-(4-methylphenylsulfonyl)ethenyl]thymidine → 3'-azido-2',3'-dideoxy-5'-O-acetyluridine (84472-87-7)

Guidance literature:

With pyrrolidine; In acetonitrile; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo501647w

Reference yield: 97.0%

5'-O-acetyl-3'-azido-3'-deoxy-3-[(Z)-2-(4-methylphenylsulfonyl)-ethenyl]thymidine → 3'-azido-2',3'-dideoxy-5'-O-acetyluridine (84472-87-7)

Guidance literature:

With sodium hydride; 1-dodecylthiol; In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo501647w

Reference yield:

Navuridine (84472-85-5) + acetic anhydride (108-24-7) → 3'-azido-2',3'-dideoxy-5'-O-acetyluridine (84472-87-7)

Guidance literature:

Heating;

DOI:10.1021/jm00385a033

upstream raw materials:

Navuridine

acetic anhydride

1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)uracil

O^5'-trityl-2'-deoxy-uridine

Downstream raw materials:

3'-Azido-2',3'-dideoxy-5-bromouridine

3'-azido-2',3'-dideoxycytidine

3'-amino-2',3'-dideoxycytidine

Acetic acid (2S,3S,5R)-3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Refernces

• 1、 Lin,Chen,McLaren,Gao,Ghazzouli,Prusoff. "Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses". . p. 440 - 444. Retrieved 2007/10/02.