trans-(+)-Tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic aid

Base Information

• Chemical Name: trans-(+)-Tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic aid
• CAS No.: 1448-96-0
• Molecular Formula: C₁₉H₃₂O₄
• Molecular Weight: 324.461
• Nikkaji Number: J56.258K
• Wikidata: Q105323696
• Mol file: 1448-96-0.mol

Synonyms:protolichesterinic acid;protolichesterinic acid, (2R-trans)-isomer;K salt;protolichesterinic acid, (2S-trans)-isomer

Chemical Property of trans-(+)-Tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic aid

Chemical Property:

• Vapor Pressure: 7.11E-11mmHg at 25°C
• Boiling Point: 488.4°Cat760mmHg
• Flash Point: 166.7°C
• PSA: 63.60000
• Density: 1.02g/cm³
• LogP: 4.86990
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 324.23005950
• Heavy Atom Count: 23
• Complexity: 389

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC1C(C(=C)C(=O)O1)C(=O)O
• Isomeric SMILES: CCCCCCCCCCCCC[C@@H]1[C@H](C(=C)C(=O)O1)C(=O)O
• Uses: (+)-Protolichesteric Acid is a lichen compound isolated from iceland moss, that exhibits anti-proliferative effect on several cancer cell lines.

Technology Process of trans-(+)-Tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic aid

There total 58 articles about trans-(+)-Tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic aid 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: 85.0%

(2R,3S,4R)-4-Benzenesulfinyl-4-methyl-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid → (+)-protolichesterinic acid (493-46-9,1448-96-0,17002-28-7,22800-27-7,51260-32-3,58845-78-6,58845-79-7,60478-54-8)

Guidance literature:

In toluene; at 110 ℃; for 1h;

DOI:10.1021/jo9606970

Reference yield: 72.0%

magnesium methyl carbonate (4861-79-4) + (2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid (244612-58-6) → (+)-protolichesterinic acid (493-46-9,1448-96-0,17002-28-7,22800-27-7,51260-32-3,58845-78-6,58845-79-7,60478-54-8)

Guidance literature:

magnesium methyl carbonate; (2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid; In N,N-dimethyl-formamide; at 135 - 140 ℃; for 70h;

With formaldehyd; sodium acetate; acetic acid; In water; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200500961

Reference yield: 72.0%

(+)-Protolichesterinsaeuremethylester (144071-11-4) → (+)-protolichesterinic acid (493-46-9,1448-96-0,17002-28-7,22800-27-7,51260-32-3,58845-78-6,58845-79-7,60478-54-8)

Guidance literature:

With hydrogenchloride; In water; butanone; for 2h; Heating;

DOI:10.1016/S0957-4166(01)00345-7

upstream raw materials:

(+)-Protolichesterinsaeuremethylester

magnesium methyl carbonate

(2R,3S)-5-oxo-2-tridecyl-tetrahydrofuran-3-carboxylic acid

(4S,5R)-5-tridecyl-4-[tris(methylsulfanyl)methyl]-4,5-dihydro-3H-furan-2-one

Downstream raw materials:

(+/-)-lichesterinic acid

(+)-lichesterinic acid

(+)-roccellaric acid

(+)-dihydroprotolichesterinic acid

Refernces

• 1、 Nallasivam, Jothi L.,Fernandes, Rodney A.. "A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin". . p. 708 - 716. Retrieved 2017.
• 2、 Ghatak, Anjan,Sarkar, Subrata,Ghosh, Subrata. "Strategic use of retro Diels-Alder reaction in the construction of β-carboxy-α-methylene-γ-lactones. Total synthesis of methylenolactocin and protolichesterinic acid". . p. 17335 - 17342. Retrieved 1997.
• 3、 Carlson,Oyler. "". . p. 4099. Retrieved 1975.
• 4、 Zeller, Mary A.,Riener, Michelle,Nicewicz, David A.. "Butyrolactone synthesis via polar radical crossover cycloaddition reactions: Diastereoselective syntheses of methylenolactocin and protolichesterinic acid". supporting information. p. 4810 - 4813. Retrieved 2015/04/27.