malyngolide

Base Information

• Chemical Name: malyngolide
• CAS No.: 71582-80-4
• Molecular Formula: C₁₆H₃₀O₃
• Molecular Weight: 270.412
• Mol file: 71582-80-4.mol

Synonyms:2H-Pyran-2-one,tetrahydro-6-(hydroxymethyl)-3-methyl-6-nonyl-, (3R-trans)-; (-)-Malyngolide;Malyngolide

Chemical Property of malyngolide

Chemical Property:

• Vapor Pressure: 3.29E-08mmHg at 25°C
• Boiling Point: 404°C at 760 mmHg
• PKA: 14.21±0.10(Predicted)
• Flash Point: 160.5°C
• PSA: 46.53000
• Density: 0.951g/cm³
• LogP: 3.83130

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of malyngolide

There total 207 articles about malyngolide 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: 90.7%

(3R,6S)-6-Hydroxymethyl-3-methyl-6-nonyl-3,6-dihydro-2H-pyran-2-one (132075-43-5) → (-)-malyngolide (71582-80-4)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethyl acetate; for 1h;

DOI:10.1039/P19900002677

Reference yield: 85.0%

(3R,6S)-6-Methoxymethoxymethyl-3-methyl-6-nonyl-tetrahydro-pyran-2-one (217443-59-9) → (-)-malyngolide (71582-80-4)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at -30 ℃;

DOI:10.1039/a703242k

Reference yield: 80.0%

(5S)-2-methyl-5-hydroxymethyltetradec-2-en-5-olide (487001-49-0) → (-)-malyngolide (71582-80-4) + (+)-2-epi-malyngolide (76023-93-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In hexane; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(02)01160-2

upstream raw materials:

(+)-2-epi-malyngolide

(5S)-5-hydroxymethyl-2-methylene-5-tetradecanolide

(3R,6S)-6-Hydroxymethyl-3-methyl-6-nonyl-3,6-dihydro-2H-pyran-2-one

(4S)-4-(3-ethoxycarbonylbutyl)-2,2-dimethyl-4-nonyl-1,3-dioxolane

Refernces

• 1、 Ichimoto,Machiya,Kirihata,Ueda. "Stereoselective synthesis of marine antibiotic (-)-malyngolide and its stereoisomers.". . p. 657 - 662. Retrieved 1990.
• 2、 Ohira, Susumu,Moritani, Masanori,Ida, Takahiro,Yamato, Masatoshi. "Novel Synthesis of (-)-Malyngolide using Reactions of Alkylidene Carbenes". . p. 1299 - 1300. Retrieved 1993.
• 3、 Mikie Kanada, Regina,Taniguchi, Takahiko,Ogasawara, Kunio. "Asymmetric hydrogen transfer protocol for a synthesis of (+)-frontalin and (-)-malyngolide". . p. 3631 - 3635. Retrieved 2000.
• 4、 Srivastava, Nikhil,Subba Reddy, Basi V.. "Biocatalytic Approach for the Total Synthesis of (-)-Malyngolide and Its C(5)-Epimer". . p. 267 - 272. Retrieved 2016/05/02.
• 5、 Carda, Miguel,Rodríguez, Santiago,Castillo, Encarnación,Bellido, Alejandro,Díaz-Oltra, Santiago,Marco, J. Alberto. "Stereoselective synthesis of (-)-malyngolide, (+)-malyngolide and (+)-tanikolide using ring-closing metathesis". . p. 857 - 864. Retrieved 2007/10/03.