3'-Azido-3'-deoxyadenosine

Base Information

• Chemical Name: 3'-Azido-3'-deoxyadenosine
• CAS No.: 58699-62-0
• Molecular Formula: C10H12 N8 O3
• Molecular Weight: 292.257
• DSSTox Substance ID: DTXSID201311797
• Nikkaji Number: J1.002.730F
• Mol file: 58699-62-0.mol

Synonyms:3'-azido-3'-deoxyadenosine;3'-deoxy-3'-azidoadenosine;Az-RA

Chemical Property of 3'-Azido-3'-deoxyadenosine

Chemical Property:

• Melting Point: 212-214 °C(Solv: water (7732-18-5))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 169.06000
• Density: g/cm³
• LogP: -0.62804
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 292.10323627
• Heavy Atom Count: 21
• Complexity: 433

Purity/Quality:

97% ^*data from raw suppliers

3'-Azido-3'-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)N=[N+]=[N-])O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)N=[N+]=[N-])O)N

Technology Process of 3'-Azido-3'-deoxyadenosine

There total 28 articles about 3'-Azido-3'-deoxyadenosine 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: 93.44%

3'-azido-2'-O-acetyl-5'-O-(p-toluoyl)-3'-deoxy-N6-benzoyladenine → 3'-Azido-3'-deoxyadenosine (58699-62-0)

Guidance literature:

With methylamine; In ethanol; at 20 ℃; for 16h;

Reference yield: 90.1%

C27H24N8O6 → 3'-Azido-3'-deoxyadenosine (58699-62-0)

Guidance literature:

With methylamine; In methanol; at 20 ℃; for 16h;

Reference yield: 90.0%

2,5-di-O-acetyl-3-azido-1-(6-chloropurin-9-yl)-β-D-1,3-dideoxyribofuranose (889126-06-1) → 3'-Azido-3'-deoxyadenosine (58699-62-0)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 20 ℃;

DOI:10.1080/15257770701493161

upstream raw materials:

Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine

9-(3'-azido-2'-O-acetyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine

3'-azido-3'-deoxy-2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine

Downstream raw materials:

3'-amino-3'-deoxyadenosine

3'-[N-(tert-butoxycarbonyl)-O-methyl-L-tyrosyl]amido-3'-deoxyinosine

puromycin

tert-butyl [(S)-1-({(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl}amino)-3-(4-methoxyphenyl)-1-oxopropan-2yl]carbamate