N6-Octanoyl

Base Information

• Chemical Name: N6-Octanoyl
• CAS No.: 77378-05-3
• Molecular Formula: C18H27N5O4
• Molecular Weight: 377.43808
• Mol file: 77378-05-3.mol

Synonyms:N6-Octanoyl;3'-Deoxy-N6-octanoyladenosine;N6-Octanoyl Cordycepin

Chemical Property of N6-Octanoyl

Chemical Property:

• PSA: 125.88000
• Density: 1.431g/cm³
• LogP: 2.41550

Purity/Quality:

97% ^*data from raw suppliers

N6-OctanoylCordycepin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A novel labelled N6-substituted Cordycepin derivative; an adenosine deaminase inhibitor.

Technology Process of N6-Octanoyl

There total 11 articles about N6-Octanoyl 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: 64.3%

cordycepin (73-03-0) + n-octanoic acid chloride (111-64-8) → N-octanoylcordycepin (77378-05-3)

Guidance literature:

With pyridine; at 60 ℃; Inert atmosphere; Reflux;

DOI:10.1016/j.ejmech.2008.05.013

Reference yield: 43.0%

9-[2,5-bis-O-(tertbutyldimethylsilyl)-3-deoxy-β-D-ribifuranosyl]-N6-biotinyladenine → N-octanoylcordycepin (77378-05-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h;

Reference yield:

((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate (71196-28-6) → N-octanoylcordycepin (77378-05-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / methanol; water / 3 h / 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

3.1: 1,2-dichloro-ethane; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.5 h / 20 °C

3.2: 4 h / 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; potassium carbonate; benzotriazol-1-ol; 1,2-dichloro-ethane; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

upstream raw materials:

cordycepin

n-octanoic acid chloride

((2S,4R,5R)-4-acetoxy-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl acetate

1,2,3,5-di-O-isopropylidene-D-xylofuranose

Refernces

• 1、 Wei,Ye,Chen,Zhong,Li,Pu,Li. "Synthesis and pharmacokinetic evaluation of novel N-acyl-cordycepin derivatives with a normal alkyl chain". experimental part. p. 665 - 669. Retrieved 2009/09/08.