(2S)-3-[(2S,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one

Base Information

• Chemical Name: (2S)-3-[(2S,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
• CAS No.: 102989-24-2
• Deprecated CAS: 159993-36-9
• Molecular Formula: C37H66 O7
• Molecular Weight: 622.927
• Wikidata: Q730429
• ChEMBL ID: CHEMBL138238
• Mol file: 102989-24-2.mol

Synonyms:Squamocin H;CHEMBL138238;(2S)-3-[(2S,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one;2(5H)-Furanone, 3-((2R,13R)-2,13-dihydroxy-13-((2R,2'R,5R,5'R)-octahydro-5'-((1R)-1-hydroxyundecyl)(2,2'-bifuran)-5-yl)tridecyl)-5-methyl-, (5S)-;Q730429

Chemical Property of (2S)-3-[(2S,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one

Chemical Property:

• Vapor Pressure: 1.19E-25mmHg at 25°C
• Melting Point: 45-48 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Boiling Point: 745.5°Cat760mmHg
• PKA: 14.46±0.20(Predicted)
• Flash Point: 220.3°C
• PSA: 105.45000
• Density: 1.054g/cm³
• LogP: 7.85790
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 25
• Exact Mass: 622.48085444
• Heavy Atom Count: 44
• Complexity: 801

Purity/Quality:

99%, ^*data from raw suppliers

ASIMICIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC(C1CCC(O1)C2CCC(O2)C(CCCCCCCCCCC(CC3=CC(=O)OC3C)O)O)O
• Isomeric SMILES: CCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@H]2CC[C@@H](O2)[C@@H](CCCCCCCCCC[C@@H](CC3=CC(=O)O[C@H]3C)O)O)O

Technology Process of (2S)-3-[(2S,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one

There total 149 articles about (2S)-3-[(2S,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one 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: 98.0%

C59H86O8 → (+)-asimicin (102989-24-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In aq. phosphate buffer; water; 1,2-dichloro-ethane; at 50 ℃; for 2h;

DOI:10.1002/chem.201805317

Reference yield: 91.0%

C49H94O7Si2 (1086569-84-7) → (+)-asimicin (102989-24-2)

Guidance literature:

With hydrogen fluoride; In tetrahydrofuran; acetonitrile; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jm801028c

Reference yield: 83.0%

(S)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-5H-furan-2-one → (+)-asimicin (102989-24-2)

Guidance literature:

With acetyl chloride; In methanol; dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo000500a

upstream raw materials:

(S)-3-((2R,13R)-2,13-Bis-(2-trimethylsilanyl-ethoxymethoxy)-13-{(2R,5R,2'R,5'R)-5'-[(R)-1-(2-trimethylsilanyl-ethoxymethoxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-tridecyl)-5-methyl-5H-furan-2-one

(S)-3-{(2R,13R)-2-Hydroxy-13-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-5H-furan-2-one

(2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde

(2R,4R,5S)-[5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

Refernces

• 1、 Sinha, Subhash C.,Sinha-Bagchi, Anjana,Yazbak, Ahmad,Keinan, Ehud. "Modular approach to Annonaceous acetogenins. Total synthesis of asimicin and bullatacin". . p. 9257 - 9260. Retrieved 1995.
• 2、 Tinsley, Jennifer M.,Roush, William R.. "Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes". . p. 10818 - 10819. Retrieved 2007/10/03.