2-Azidoadenosine

Base Information

• Chemical Name: 2-Azidoadenosine
• CAS No.: 59587-07-4
• Molecular Formula: C10H12N8O4
• Molecular Weight: 308.256
• Mol file: 59587-07-4.mol

Synonyms:2-Azido-D-adenosine;(4S,2R,3R,5R)-2-[6-Amino-2-(diazoazamvinyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol;NSC 36905;AC1LABXO;(2R,3R,4S,5R)-2-(6-Amino-2-azidopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;

Chemical Property of 2-Azidoadenosine

Chemical Property:

• Appearance/Colour: Off-white to grey solid
• Melting Point: 170-172 °C
• PSA: 189.29000
• LogP: -1.00424
• Storage Temp.: -20°C Freezer

Purity/Quality:

99% ^*data from raw suppliers

2-AzidoAdenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Azidoadenosine is a useful synthetic intermediate for making potent and selective coronary vasodilators.

Technology Process of 2-Azidoadenosine

There total 11 articles about 2-Azidoadenosine 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: 89.0%

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-azido-6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester (174500-37-9) → 2-Azidoadenosine (59587-07-4)

Guidance literature:

With ammonia; In ethanol; at 30 ℃; for 48h;

DOI:10.1016/0960-894X(95)00548-8

Reference yield: 61.0%

2-Chloroadenosine (146-77-0) → 2-Azidoadenosine (59587-07-4)

Guidance literature:

2-Chloroadenosine; With hydrazine hydrate; at 20 ℃; for 16h;

With acetic acid; sodium nitrite; In water; for 1h; cooling;

DOI:10.1002/ejoc.200300274

Reference yield:

→ 2-Azidoadenosine (59587-07-4)

Guidance literature:

With acetic acid; sodium nitrite;

DOI:10.1021/ja01547a068

upstream raw materials:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-azido-6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester

2-Chloroadenosine

2-hydrazinoadenosine

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Refernces

• 1、 Lioux, Thierry,Gosselin, Gilles,Mathe, Christophe. "Azido/Tetrazole Tautomerism in 2-Azidoadenine β -D-Pentofuranonucleoside Derivatives". . p. 3997 - 4002. Retrieved 2007/10/03.
• 2、 Higashiya, Seiichiro,Kaibara, Chitose,Fukuoka, Koichiro,Suda, Fuminori,Ishikawa, Masahide,Yoshida, Masasuke,Hata, Tsujiaki. "A facile synthesis of 2-azidoadenosine derivatives from guanosine as photoaffinity probes". . p. 39 - 42. Retrieved 2007/10/03.