Roccellaric acid

Base Information

• Chemical Name: Roccellaric acid
• CAS No.: 19464-85-8
• Molecular Formula: C19H34O4
• Molecular Weight: 326.47086
• Mol file: 19464-85-8.mol

Synonyms:(2R,3S,4S)-4-methyl-5-oxo-2-tridecyltetrahydrofuran-3-carboxylic acid;(+)-Roccellarsaeure;(+)-Rocellaric acid;(3S,4S,5R)-rocellaric acid;(2R,3S,4S)-4-Methyl-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid;(+)-Roccellaric acid;(-)-roccellaric acid;

Chemical Property of Roccellaric acid

Chemical Property:

• PSA: 63.60000
• LogP: 4.94980

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Roccellaric acid

There total 68 articles about Roccellaric acid 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: 100.0%

(2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid (244612-58-6) + methyl iodide (74-88-4) → (+)-roccellaric acid (19464-85-8)

Guidance literature:

(2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201001419

Reference yield: 93.0%

(3S,4S,5R)-3-methyl-5-tridecyl-4-[tris(methylsulfanyl)methyl]-4,5-dihydro-3H-furan-2-one (897657-58-8) → (+)-roccellaric acid (19464-85-8)

Guidance literature:

With boron trifluoride diethyl etherate; mercury(II) oxide; In tetrahydrofuran; water; at 20 ℃; for 3h;

DOI:10.1002/ejoc.200500961

Reference yield: 90.0%

(3S,4S,5R)-4-((1S)-1,2-dihydroxyethyl)-3-methyl-5-tridecyldihydrofuran-2-one (180267-10-1) → (+)-roccellaric acid (19464-85-8)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/jo9606970

upstream raw materials:

(+)-protolichesterinic acid

(3S,4S,5R)-3-Methyl-4--5-tridecyl-4,5-dihydro-2(3H)-furanone

(3S,4S,5R)-4-((1S)-1,2-dihydroxyethyl)-3-methyl-5-tridecyldihydrofuran-2-one

(2S,3R,4R)-4-Methyl-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Refernces

• 1、 Sarkale, Abhijeet M.,Maurya, Vidyasagar,Giri, Sachin,Appayee, Chandrakumar. "Stereodivergent Synthesis of Chiral Paraconic Acids via Dynamic Kinetic Resolution of 3-Acylsuccinimides". supporting information. p. 4266 - 4270. Retrieved 2019/06/18.
• 2、 Blanc, Delphine,Madec, Jonathan,Popowyck, Florence,Ayad, Tahar,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie,Genet, Jean-Pierre. "General enantioselective synthesis of butyrolactone natural products via ruthenium-SYNPHOS-catalyzed hydrogenation reactions". . p. 943 - 950. Retrieved 2008/03/27.