(+)-euryfuran

Base Information

• Chemical Name: (+)-euryfuran
• CAS No.: 67919-45-3
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.339
• Mol file: 67919-45-3.mol

Synonyms:(+)-euryfuran

Chemical Property of (+)-euryfuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-euryfuran

There total 49 articles about (+)-euryfuran 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: 40.0%

Dithiocarbonic acid S-methyl ester O-((5S,5aS,9aS)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-5-yl) ester (137644-74-7) → (+/-)-euryfuran (50490-43-2,67919-45-3,69780-10-5,78853-99-3,79895-94-6,137695-43-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃;

DOI:10.3987/COM-91-5794

Reference yield:

(+)-confertifoline (1811-23-0) → (+)-euryfuran (67919-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether / Ambient temperature

2: 70 percent / pyridinium chlorochromate

With lithium aluminium tetrahydride; pyridinium chlorochromate; In diethyl ether;

Reference yield:

(4,4-Dimethyl-4,5,6,7-tetrahydro-isobenzofuran-1-yl)-methanol (137644-71-4) → (+/-)-euryfuran (50490-43-2,67919-45-3,69780-10-5,78853-99-3,79895-94-6,137695-43-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / benzene / 6 h / Ambient temperature

2: 88 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 83 °C

3: 26 percent / o-xylene / 3 h / 100 °C

4: 79 percent / lithium triethylhydroborate / tetrahydrofuran; hexane / 14 h / Ambient temperature

5: 98 percent / DMSO, triethylamine, sulfur trioxide pyridine complex / CH₂Cl₂ / 2 h / 0 °C

6: 63 percent / tris(triphenylphosphine)rhodium(I) chloride / benzene / 1 h / Heating

7: hydrogen / 10percent palladium on carbon / ethyl acetate / 10 h / Ambient temperature

With sodium hydroxide; Wilkinson's catalyst; potassium tert-butylate; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sulfur trioxide pyridine complex; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; o-xylene; ethyl acetate; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4020(01)85635-0

upstream raw materials:

(+)-confertifoline

(5aR,9aR)-3-Butylsulfanyl-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan

4,6,7,8,9,9a-hexahydro-6,6,9a-trimethylnaphtho<1,2-c>-furan

Dithiocarbonic acid S-methyl ester O-((5S,5aS,9aS)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-5-yl) ester

Downstream raw materials:

3,6-dihydroxy-2-(6',6',9'a-trimethyl-4',5',5'aS,6',7',8',9',9'aS-octahydronaphtho[1,2-c]furan-3'-yl)-benzaldehyde

(+/-)-confertifolin

(+)-confertifoline

Methyl 2,5-dihydroxybenzoate

Refernces

• 1、 Kanematsu, Ken,Soejima, Seizo. "TOTAL SYNTHESIS OF EURYFURAN VIA TWO SEQUENTIAL FURAN RING TRANSFER REACTION". . p. 1483 - 1486. Retrieved 2007/10/02.
• 2、 Nakano, Tatsuhiko,Maillo, Maria Aracelis. "Reaction of (1S,6S)-1,7,7-Trimethyl-2,3-dimethylene-trans-bicyclodecane with Thallium(III) Acetate; a New Route to (-)-Warburganal and (+)-Euryfuran". . p. 2137 - 2140. Retrieved 2007/10/02.