(5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone

Base Information

• Chemical Name: (5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone
• CAS No.: 1580541-78-1
• Molecular Formula: C₂₅H₃₄O₆
• Molecular Weight: 430.541
• Mol file: 1580541-78-1.mol

Synonyms:(5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone

Chemical Property of (5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone

There total 13 articles about (5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone 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: 80.0%

(1'R,5E)-1'-[2'',5''-bis(methoxymethoxy)phenyl]prop-2-en-1-yl-6,10-dimethyl-2-methylideneundeca-5,9-dienoate (1580541-77-0) → (5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone (1580541-78-1)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 8h; Reagent/catalyst;

DOI:10.1002/ejoc.201301269

Reference yield:

1-chloro-3,7-dimethylocta-2,6-diene (5389-87-7) → (5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone (1580541-78-1)

Guidance literature:

Multi-step reaction with 5 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

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; N-ethyl-N,N-diisopropylamine; In diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 4.1: |Yamaguchi Lactonization;

DOI:10.1002/ejoc.201301269

Reference yield:

2,5-Dihydroxybenzaldehyde (1194-98-5) → (5R,3''E)-5-[2',5'-bis(methoxymethoxyphenyl)]-3-(4'',8''-dimethylnona-3'',7''-dien-1''-yl)-2(5H)-furanone (1580541-78-1)

Guidance literature:

Multi-step reaction with 9 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

With Grubbs catalyst first generation; dmap; methanesulfonamide; 2,4,6-trichlorobenzoyl chloride; AD-mix-α; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 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

Downstream raw materials:

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

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.