3'-Azido-2',3'-dideoxyadenosine

Base Information

• Chemical Name: 3'-Azido-2',3'-dideoxyadenosine
• CAS No.: 66323-44-2
• Molecular Formula: C10H12N8O2
• Molecular Weight: 276.258
• Hs Code.: 2934999090
• Mol file: 66323-44-2.mol

Synonyms:3'-Azido-2',3'-dideoxyadenosine;3'-Azido-ddA;3'-AzddAdo;3'-N3-ddA;AZA;[(2S,3S,5R)-5-(6-Aminopurin-9-yl)-3-azidooxolan-2-yl]methanol;

Chemical Property of 3'-Azido-2',3'-dideoxyadenosine

Chemical Property:

• Melting Point: 186-187 °C
• PSA: 148.83000
• LogP: 0.40116

Purity/Quality:

97% ^*data from raw suppliers

3'-Azido-2',3'-dideoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3'-Azido-2',3'-dideoxyadenosine

There total 12 articles about 3'-Azido-2',3'-dideoxyadenosine 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: 90.0%

9-(3-O-mesyl-2-deoxy-β-D-threo-pentofuranosyl)adenine (110143-04-9) → 9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)adenine (66323-44-2)

Guidance literature:

With lithium azide; In N,N-dimethyl-formamide; at 80 ℃; for 4h;

DOI:10.1021/jm00394a034

Reference yield: 88.0%

Benzoic acid (2S,3S,5R)-5-(6-amino-purin-9-yl)-3-azido-tetrahydro-furan-2-ylmethyl ester (115913-74-1) → 9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)adenine (66323-44-2)

Guidance literature:

With ammonia; In methanol;

DOI:10.1021/jm00118a033

Reference yield:

9-(2'-deoxy-β-D-threo-ribofuranosyl)-adenine (13276-53-4,7005-15-4) → 9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)adenine (66323-44-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / pyridine; dimethylformamide / 4 °C

2: 68 percent / LiN₃, Ph₃P / dimethylformamide; various solvent(s) / 24 h / Ambient temperature

3: 88 percent / NH₃ / methanol

With lithium azide; ammonia; triphenylphosphine; In pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00118a033

upstream raw materials:

N6-Benzoyl-9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)adenine

9-(3-O-mesyl-2-deoxy-β-D-threo-pentofuranosyl)adenine

Benzoic acid (2S,3S,5R)-5-(6-amino-purin-9-yl)-3-azido-tetrahydro-furan-2-ylmethyl ester

N⁶-octanoyladenine

Downstream raw materials:

9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine

Refernces

• 1、 Herdewijn, Piet A. M.. "Anchimeric Assistance of a 5'-O-Carbonyl Function for Inversion of Configuration at the 3'-Carbon Atom of 2'-Deoxyadenosine. Synthesis of 3'-Azido-2',3'-dideoxyadenosine and 3'-Azido-2',3'-dideoxyinosine". . p. 5050 - 5053. Retrieved 2007/10/02.
• 2、 Herdewijn,Pauwels,Baba,Balzarini,De Clercq. "Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: A structure-activity analysis". . p. 2131 - 2137. Retrieved 2007/10/02.