(+)-Eudesmin

Base Information

• Chemical Name: (+)-Eudesmin
• CAS No.: 29106-36-3
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445
• European Community (EC) Number: 637-069-7
• UNII: 3TPV0HJ9B0
• DSSTox Substance ID: DTXSID50951699
• Nikkaji Number: J276.914J
• Wikidata: Q27105196
• Metabolomics Workbench ID: 67901
• ChEMBL ID: CHEMBL519099
• Mol file: 29106-36-3.mol

Synonyms:eudesmin

Chemical Property of (+)-Eudesmin

Chemical Property:

• Melting Point: 107-108℃
• Boiling Point: 517.3±50.0 °C(Predicted)
• PSA: 55.38000
• Density: 1.173±0.06 g/cm3(Predicted)
• LogP: 3.79620
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 386.17293854
• Heavy Atom Count: 28
• Complexity: 457

Purity/Quality:

98% ^*data from raw suppliers

(+)-Eudesmin 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC)OC)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)OC)OC)OC

Technology Process of (+)-Eudesmin

There total 37 articles about (+)-Eudesmin 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: 90.0%

1-(3,4-dimethoxyphenyl)-1-(3-(3,4-dimethoxyphenyl)-2-propenyloxy)-2,3-epoxypropane (438581-68-1) → (+/-)-dimethylpinoresinol (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8)

Guidance literature:

1-(3,4-dimethoxyphenyl)-1-(3-(3,4-dimethoxyphenyl)-2-propenyloxy)-2,3-epoxypropane; With [Cp₂TiCl]; In tetrahydrofuran; at 60 ℃;

With iodine; In tetrahydrofuran; at 60 ℃; Further stages.;

DOI:10.1021/jo010857u

Reference yield: 55.0%

(3S,3aS,6S,6aS)-3,6-Bis-(3,4-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-diol (911858-80-5) → eudesmin (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.tetlet.2006.06.127

Reference yield: 51.0%

(3R,3aR,6R,6aR)-3,6-Bis-(3,4-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-diol → eudesmine (526-06-7,4375-03-5,16499-02-8,25305-05-9,29106-36-3,38609-26-6,38759-91-0,60102-89-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.tetlet.2006.06.127

upstream raw materials:

dimethyl sulfate

pinoresinol

diazomethane

pinoresinol

Downstream raw materials:

(2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol

(+)-epipinoresinol dimethyl ether

(3aR)-1c,4c-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan

(+/-)-1c,4c-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan

Refernces

• 1、 Kise, Naoki,Fujimoto, Azumi,Moriyama, Noriaki,Ueda, Nasuo. "Stereoselective intramolecular coupling of diaroylacetates of (1R,1′R)-exo,exo′-3,3′-biisoborneol by oxidation with Br 2". . p. 2495 - 2497. Retrieved 2007/10/03.
• 2、 Roy, Subhas Chandra,Rana, Kalyan Kumar,Guin, Chandrani. "Short and stereoselective total synthesis of furano lignans (±)-dihydrosesamin, (±)-lariciresinol dimethyl ether, (±)-acuminatin methyl ether, (±)-sanshodiol methyl ether, (±)-lariciresinol, (±)-acuminatin, and (±)-lariciresinol". . p. 3242 - 3248. Retrieved 2007/10/03.