Zeaenol

Base Information

• Chemical Name: Zeaenol
• CAS No.: 66018-41-5
• Molecular Formula: C19H24O7
• Molecular Weight: 364.39
• Mol file: 66018-41-5.mol

Synonyms:Antibiotic LL Z1640-4;

Chemical Property of Zeaenol

Chemical Property:

• Boiling Point: 636.3±55.0 °C(Predicted)
• PKA: 7.43±0.70(Predicted)
• PSA: 116.45000
• Density: 1.275±0.06 g/cm3(Predicted)
• LogP: 1.39200
• Storage Temp.: -20C

Purity/Quality:

98% ^*data from raw suppliers

AntibioticLLZ1640-4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: LL Z1640-4 is a cis-enol resorcylic acid lactone first reported in 1978 exhibiting both antiviral and antiprotozoan activity. More recently, LL Z1640-2, containing the essential cis-enone system that selectively inhibits TAK 1, has gained literature focus. With its "inactive" cis-enol, LL Z1640-4 is an ideal negative control to help dissect the selectivity of the MAP kinases.

Technology Process of Zeaenol

There total 90 articles about Zeaenol 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: 94.0%

(3aS,4E,7S,14E,17S,17aS)-10-hydroxy-12-methoxy-17-(methoxymethoxy)-2,2,7-trimethyl-6,7,17,17a-tetrahydro-3aH-benzo[c][1,3]dioxolo[4,5-i][1]oxacyclotetradecin-9(16H)-one → zeaenol (66018-41-5,69427-14-1)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; for 24h;

DOI:10.1016/j.tet.2015.06.035

Reference yield: 92.0%

cochliomycin A → zeaenol (66018-41-5,69427-14-1)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; for 20h;

DOI:10.1002/ejoc.201200241

Reference yield: 91.0%

cochliomycin B (1278520-08-3) → zeaenol (66018-41-5,69427-14-1)

Guidance literature:

With acetyl chloride; In methanol; for 10h; Inert atmosphere;

DOI:10.1002/ejoc.201301613

upstream raw materials:

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

2-hydroxy-4-methoxy-6-vinylbenzaldehyde

(4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

Refernces

• 1、 Doda, Sai Reddy,Raghavendar, Avula,Haridasyam, Sharath Babu,Putta, Chandra Shekar,Rao, Bhattu Kanakadurga,Kadari, Sudhakar. "Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol". . p. 78 - 84. Retrieved 2019/06/06.
• 2、 Kumar, Rayala Naveen,Meshram. "Convergent and stereoselective synthesis of (-)-zeaenol". . p. 5669 - 5677. Retrieved 2015/08/03.