5'-AZIDO-5'-DEOXYTHYMIDINE

Base Information

• Chemical Name: 5'-AZIDO-5'-DEOXYTHYMIDINE
• CAS No.: 19316-85-9
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.244
• Mol file: 19316-85-9.mol

Synonyms:5'-Azido-5'-deoxythymidine;NSC 254064;

Chemical Property of 5'-AZIDO-5'-DEOXYTHYMIDINE

Chemical Property:

• Melting Point: 164-166℃
• PSA: 134.07000
• LogP: -0.74354

Purity/Quality:

99% ^*data from raw suppliers

5’-Azido-(5’-deoxy)thymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5’Azido-(5’deoxy)thymidine is a potential thymidine-based inhibitor of mycobacterium tuberculosis monophosphate kinase (TMPKmt), an essential enzyme to DNA replication of tuberculosis mycobacterium.

Technology Process of 5'-AZIDO-5'-DEOXYTHYMIDINE

There total 25 articles about 5'-AZIDO-5'-DEOXYTHYMIDINE 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: 99.0%

5'-O-(p-toluenesulfonyl)thymidine (7253-19-2) → 5'-azido-5'-deoxythymidine (19316-85-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1080/15257770.2018.1514122

Reference yield: 91.0%

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 5'-azido-5'-deoxythymidine (19316-85-9)

Guidance literature:

With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate; In N,N-dimethyl-formamide; toluene; at 40 ℃; for 2h;

DOI:10.1021/jm00108a028

Reference yield: 90.0%

1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (25953-14-4,94892-66-7) → 5'-azido-5'-deoxythymidine (19316-85-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 17h;

DOI:10.1039/c9ob01133a

upstream raw materials:

3'-O-acetyl-5'-azido-5'-deoxythymidine

5’-chloro-5’-deoxythymidine

5'-O-(p-toluenesulfonyl)thymidine

thymidine

Downstream raw materials:

5'-N-(4-methoxytrityl)-5'-amino-5'-deoxy-thymidine

5'-monomethoxytritylamino-2',5'-dideoxythymidine-3'-O-succinate

Succinic acid (2R,3S,5R)-2-({[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 4-nitro-phenyl ester

9-<2-Deoxy-3-O-methanesulphonyl-5-O-(4-monomethoxytrityl)-β-D-threo-pentofuranosyl>adenine

Refernces

• 1、 Godeau, Guilhem,Brun, Christophe,Arnion, Hélène,Staedel, Cathy,Barthélémy, Philippe. "Glycosyl-nucleoside fluorinated amphiphiles as components of nanostructured hydrogels". . p. 1012 - 1015. Retrieved 2010.
• 2、 Mattarella, Martin,Berstis, Laura,Baldridge, Kim K.,Siegel, Jay S.. "Synthesis of bioconjugated sym -pentasubstituted corannulenes: Experimental and theoretical investigations of supramolecular architectures". . p. 115 - 128. Retrieved 2014.
• 3、 Schwekendiek, Kirsten,Kobarg, Hauke,Daumlechner, Lena,Soennichsen, Frank D.,Lindhorst, Thisbe K.. "Photodimerisation of glycothymidines in solution and in micelles". . p. 9399 - 9401. Retrieved 2011.
• 4、 Black, David StC,Das, Theerthankar,Kumar, Naresh,Rice, Scott A.,Sabir, Shekh,Subramoni, Sujatha. "Design, Synthesis and Biological Evaluation of Novel Anthraniloyl-AMP Mimics as PQS Biosynthesis Inhibitors against Pseudomonas aeruginosa Resistance". . . Retrieved 2020/07/25.
• 5、 Michalska, Lucyna,Wawrzyniak, Dariusz,Szymańska-Michalak, Agnieszka,Barciszewski, Jan,Boryski, Jerzy,Baraniak, Dagmara. "Synthesis and biological assay of new 2’-deoxyuridine dimers containing a 1,2,3-triazole linker. Part I". . p. 218 - 235. Retrieved 2019/01/04.