atpenin A4

Base Information

• Chemical Name: atpenin A4
• CAS No.: 119509-25-0
• Molecular Formula: C₁₅H₂₂ClNO₅
• Molecular Weight: 331.796
• Mol file: 119509-25-0.mol

Synonyms:2(1H)-Pyridinone,3-(5-chloro-2,4-dimethyl-1-oxohexyl)-4-hydroxy-5,6-dimethoxy-,[2S-(2R*,4R*,5R*)]-; Antibiotic FO 125A4; Atpenin A 4; FO 125A4

Chemical Property of atpenin A4

Chemical Property:

• Vapor Pressure: 4.48E-12mmHg at 25°C
• Boiling Point: 499.6°Cat760mmHg
• Flash Point: 255.9°C
• PSA: 88.88000
• Density: 1.23g/cm³
• LogP: 2.98230

Purity/Quality:

ATPENIN A4 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of atpenin A4

There total 7 articles about atpenin A4 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: 97.0%

(2S,4S,5S)-5-chloro-1-(5,6-dimethoxy-2,4-di(methoxymethoxy)pyridin-3-yl)-2,4-dimethylhexan-1-one → atpenin A4 (119509-25-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1248/cpb.c12-00266

Reference yield:

C17H38O3Si (1184940-23-5) → atpenin A4 (119509-25-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: trimethylamine hydrochloride; triethylamine; p-toluenesulfonyl chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere

1.2: 0.5 h / -78 - 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.1: N-chloro-succinimide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

8.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With N-chloro-succinimide; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; trimethylamine hydrochloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1248/cpb.c12-00266

Reference yield:

C17H37ClOSi → atpenin A4 (119509-25-0)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C / Inert atmosphere

3: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere

4: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

5: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1248/cpb.c12-00266

upstream raw materials:

C₁₇H₃₈O₃Si

Refernces