4aα-Formyl-1-methyl-8-methylenegibbane-1α,10β-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: 4aα-Formyl-1-methyl-8-methylenegibbane-1α,10β-dicarboxylic acid dimethyl ester
• CAS No.: 19427-33-9
• Molecular Formula: C22H30O5
• Molecular Weight: 374.4706
• Mol file: 19427-33-9.mol

Synonyms:4aα-Formyl-1-methyl-8-methylenegibbane-1α,10β-dicarboxylic acid dimethyl ester

Chemical Property of 4aα-Formyl-1-methyl-8-methylenegibbane-1α,10β-dicarboxylic acid dimethyl ester

Chemical Property:

• Melting Point: 94 - 95 °C
• PSA: 69.67000
• LogP: 3.31650

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4aα-Formyl-1-methyl-8-methylenegibbane-1α,10β-dicarboxylic acid dimethyl ester

There total 8 articles about 4aα-Formyl-1-methyl-8-methylenegibbane-1α,10β-dicarboxylic acid dimethyl ester 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:

C20H25ClO3 → Gibberellin A 24-dimethylester (19427-33-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diethyl ether / 16 h / 0 - 18 °C

2.1: bis(N-tert-butylsalicylaldiminato)copper(II) / tetrahydrofuran; cyclohexane / 2 h / 90 °C

3.1: lithium; ammonia / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C

3.2: 5 h / 0 °C

4.1: potassium hexamethylsilazane; oxygen / tetrahydrofuran; N,N-dimethyl-formamide; toluene / 3 h / 0 °C

5.1: diethyl ether

With bis(N-tert-butylsalicylaldiminato)copper(II); ammonia; oxygen; lithium; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; cyclohexane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/acs.joc.8b00876

Reference yield:

C21H26N2O3 → Gibberellin A 24-dimethylester (19427-33-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bis(N-tert-butylsalicylaldiminato)copper(II) / tetrahydrofuran; cyclohexane / 2 h / 90 °C

2.1: lithium; ammonia / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C

2.2: 5 h / 0 °C

3.1: potassium hexamethylsilazane; oxygen / tetrahydrofuran; N,N-dimethyl-formamide; toluene / 3 h / 0 °C

4.1: diethyl ether

With bis(N-tert-butylsalicylaldiminato)copper(II); ammonia; oxygen; lithium; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; cyclohexane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/acs.joc.8b00876

Reference yield:

methyl (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-1-methyl-8-methylene-2,7-bis((methylsulfonyl)oxy)-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate (91298-28-1) → Gibberellin A 24-dimethylester (19427-33-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium; ammonia / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C

2.1: pyridine; oxalyl dichloride / diethyl ether; N,N-dimethyl-formamide / 24 h / 0 - 18 °C

3.1: diethyl ether / 16 h / 0 - 18 °C

4.1: bis(N-tert-butylsalicylaldiminato)copper(II) / tetrahydrofuran; cyclohexane / 2 h / 90 °C

5.1: lithium; ammonia / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C

5.2: 5 h / 0 °C

6.1: potassium hexamethylsilazane; oxygen / tetrahydrofuran; N,N-dimethyl-formamide; toluene / 3 h / 0 °C

7.1: diethyl ether

With pyridine; oxalyl dichloride; bis(N-tert-butylsalicylaldiminato)copper(II); ammonia; oxygen; lithium; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; cyclohexane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/acs.joc.8b00876

upstream raw materials:

diazomethane

methyl (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-1-methyl-8-methylene-2,7-bis((methylsulfonyl)oxy)-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate

(1R,4bR,7R,9aR,10S,10aS)-10-(methoxycarbonyl)-1-methyl-8-methylene-2,3,4b,5,6,7,8,9,10,10a-decahydro-1H-7,9a-methanobenzo[a]azulene-1-carboxylic acid

Refernces