GanoMycin I

Base Information

• Chemical Name: GanoMycin I
• CAS No.: 1191255-15-8
• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.435
• Mol file: 1191255-15-8.mol

Synonyms:(R,E)-5-(2,5-dihydroxyphenyl)-3-(4,8-dimethylnona-3,7-dien-1-yl)furan-2(5Η)-one

Chemical Property of GanoMycin I

Chemical Property:

• Boiling Point: 521.5±50.0 °C(Predicted)
• PKA: 9.68±0.48(Predicted)
• Density: 1.135±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

GanomycinI 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of GanoMycin I

There total 15 articles about GanoMycin I 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: 85.0%

(5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone (1580541-78-1) → (R,E)-5-(2,5-dihydroxyphenyl)-3-(4,8-dimethylnona-3,7-dien-1-yl)furan-2(5Η)-one (1191255-15-8)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; at 20 ℃; for 18h;

DOI:10.1002/ejoc.201301269 DOI:10.1002/ejoc.201301269

Reference yield:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → (R,E)-5-(2,5-dihydroxyphenyl)-3-(4,8-dimethylnona-3,7-dien-1-yl)furan-2(5Η)-one (1191255-15-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / hexane; diethyl ether / 22 h / 20 °C

1.2: 1 h / -78 - 20 °C

2.1: manganese(IV) oxide / hexane / 6 h / 20 °C

3.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol; water / 1 h / 20 °C

4.1: N-ethyl-N,N-diisopropylamine; dmap; 2,4,6-trichlorobenzoyl chloride / toluene / 8 h

5.1: Grubbs catalyst first generation / dichloromethane / 8 h / 20 °C

6.1: toluene-4-sulfonic acid / ethanol / 18 h / 20 °C

With Grubbs catalyst first generation; dmap; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; N,N,N,N,-tetramethylethylenediamine; 2,4,6-trichlorobenzoyl chloride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In diethyl ether; ethanol; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 4.1: |Yamaguchi Lactonization;

DOI:10.1002/ejoc.201301269

Reference yield:

2,5-Dihydroxybenzaldehyde (1194-98-5) → (R,E)-5-(2,5-dihydroxyphenyl)-3-(4,8-dimethylnona-3,7-dien-1-yl)furan-2(5Η)-one (1191255-15-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / acetone / 10 h / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 1 h / 0 °C

3.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 - 0 °C

4.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 10 h / 0 - 20 °C

5.1: AD-mix-α; methanesulfonamide / tert-butyl alcohol; water / 12 h / 0 °C

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -78 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h

8.1: N-ethyl-N,N-diisopropylamine; dmap; 2,4,6-trichlorobenzoyl chloride / toluene / 8 h

9.1: Grubbs catalyst first generation / dichloromethane / 8 h / 20 °C

10.1: toluene-4-sulfonic acid / ethanol / 18 h / 20 °C

With Grubbs catalyst first generation; dmap; methanesulfonamide; 2,4,6-trichlorobenzoyl chloride; AD-mix-α; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetone; toluene; mineral oil; tert-butyl alcohol; 2.2: |Horner-Wadsworth-Emmons Olefination / 7.1: |Smiles Aromatic Rearrangement / 8.1: |Yamaguchi Lactonization;

DOI:10.1002/ejoc.201301269

upstream raw materials:

2,5-Dihydroxybenzaldehyde

2,5-bis(methoxymethoxy)benzaldehyde

ethyl (E)-3-[2,5-bis(methoxymethoxy)phenyl]prop-2-enoate

(E)-3-[2,5-bis(methoxymethoxy)phenyl]prop-2-en-1-ol

Refernces

• 1、 Yajima, Arata,Urao, Shota,Katsuta, Ryo,Nukada, Tomoo. "Concise Syntheses and Biological Activities of Ganomycin i and Fornicin A". . p. 731 - 738. Retrieved 2015/10/05.