4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol

Base Information

• Chemical Name: 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol
• CAS No.: 78919-28-5
• Molecular Formula: C20H22O5
• Molecular Weight: 342.392
• DSSTox Substance ID: DTXSID001120689
• Nikkaji Number: J1.891.603G
• Wikidata: Q105132674
• Mol file: 78919-28-5.mol

Synonyms:chicanine

Chemical Property of 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol

Chemical Property:

• Boiling Point: 483.8±45.0 °C(Predicted)
• PKA: 9.91±0.35(Predicted)
• PSA: 57.15000
• Density: 1 +-.0.06 g/cm3(Predicted)
• LogP: 4.21430
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 342.14672380
• Heavy Atom Count: 25
• Complexity: 457

Purity/Quality:

≥98% ^*data from raw suppliers

Chicanin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(OC1C2=CC3=C(C=C2)OCO3)C4=CC(=C(C=C4)O)OC)C
• Isomeric SMILES: C[C@@H]1[C@@H]([C@@H](O[C@H]1C2=CC3=C(C=C2)OCO3)C4=CC(=C(C=C4)O)OC)C
• Uses: Chicanin is a compound isolated from the fruit of Schisandra sphenanthera which shows moderate inhibition of herpes simplex virus-2 and adenovirus in human hepatocellular carcinoma and African green monkey kidney cell.

Technology Process of 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol

There total 18 articles about 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol 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: 77.0%

4-((2S,3R,4S,5S)-5-(benzo[d][1,3]dioxol-5-yl)-3,4-dimethyltetrahydrofuran-2-yl)-2-methoxyphenyl 4-methylbenzenesulfonate (1310802-75-5) → (+)-chicanine (78919-28-5)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 20 ℃; for 15h;

DOI:10.1016/j.tetlet.2011.03.154

Reference yield: 56.0%

C27H26O6 (1310802-74-4) → (+)-chicanine (78919-28-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2011.03.154

Reference yield: 35.0%

C27H28O5 (1310802-72-2) → (+)-chicanine (78919-28-5)

Guidance literature:

With palladium on carbon; hydrogen; In benzene;

DOI:10.1016/j.tetlet.2011.03.154

upstream raw materials:

(2R,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-methylpropan-1-ol

(2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutan-1-ol

(2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal

(1R,2S,3R,4S)-1-(benzo[d][1,3]dioxol-5-yl)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutan-1-ol

Downstream raw materials:

4-(4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol

desoxydemethylenechicanine

Macelignan

desoxyenshicine

Refernces

• 1、 Harada, Kenichi,Horiuchi, Hiroki,Tanabe, Kazuma,Carter, Rich G.,Esumi, Tomoyuki,Kubo, Miwa,Hioki, Hideaki,Fukuyama, Yoshiyasu. "Asymmetric synthesis of (-)-chicanine using a highly regioselective intramolecular Mitsunobu reaction and revision of its absolute configuration". . p. 3005 - 3008. Retrieved 2011/06/23.