Antibiotic 704III

Base Information

• Chemical Name: Antibiotic 704III
• CAS No.: 58801-71-1
• Molecular Formula: C14H18O4
• Molecular Weight: 250.29
• Mol file: 58801-71-1.mol

Synonyms:(R)-methyl 5-[(E,E)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-carboxylate;(+)-gregatin B;gregatin B;methyl {(R)-5-[(E,E)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl}carboxylate;(R)-2-[(E,E)-hexa-1,3-dienyl]-4-(methoxycarbonyl)-2,5-dimethylfuran-3(2H)-one;

Chemical Property of Antibiotic 704III

Chemical Property:

• PSA: 52.60000
• LogP: 2.31380

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Antibiotic 704III

There total 52 articles about Antibiotic 704III 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%

2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1301680-12-5) + methyl (E)-(5R)-5-(2-iodovinyl)-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-carboxylate → methyl {(R)-5-[(E,E)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl}carboxylate (58801-71-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 10 ℃; for 13h; Inert atmosphere;

DOI:10.1021/ol402472q

Reference yield: 78.0%

methyl (E,E)-(R)-4-acetoxy-4-methyl-3-oxodeca-5,7-dienoate (1402731-45-6) → methyl {(R)-5-[(E,E)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl}carboxylate (58801-71-1) + methyl {(R)-5-[(1'E,3'Z)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl}carboxylate (1402731-59-2)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.201200207

Reference yield: 61.0%

methyl (E)-(R)-4-hydroxy-4-methyl-3-oxodeca-5,7-dienoate + acetyl chloride (75-36-5) → methyl {(R)-5-[(E,E)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl}carboxylate (58801-71-1)

Guidance literature:

methyl (E)-(R)-4-hydroxy-4-methyl-3-oxodeca-5,7-dienoate; With triethylamine; In dichloromethane; at 20 ℃; for 0.0833333h; Inert atmosphere;

acetyl chloride; In dichloromethane; at 20 ℃; for 1.08333h; Inert atmosphere;

DOI:10.1002/ejoc.201200207

upstream raw materials:

diazomethane

3-acetyl-5-<(1E,3E)-hexa-1,3-dienyl>-4-hydroxy-5-methylfuran-2(5H)-one

mevalonic acid

methyl 2,5-dihydroxy-2-methylpentanoate

Downstream raw materials:

methyl {(S)-5-[(E,E)-hexa-1,3-dienyl]-2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl}carboxylate

(?)-graminin A

Refernces

• 1、 Ito, Yoichi,Kusakabe, Taichi,Dhage, Yogesh Daulat,Takahashi, Keisuke,Sakata, Ken,Sasai, Hiroaki,Kato, Keisuke. "Total Synthesis of (-)-Graminin A Based on Asymmetric Cyclization Carbonylation of Propargyl Acetate". . p. 16268 - 16277. Retrieved 2019/12/27.
• 2、 Burghart-Stoll, Heike,Brueckner, Reinhard. "Total syntheses of the gregatins A-D and aspertetronin A: Structure revisions of these compounds and of aspertetronin B, together with plausible structure revisions of gregatin E, cyclogregatin, graminin A, the penicilliols A and B, and the huaspenones A and B". . p. 3978 - 4017. Retrieved 2012/10/18.