(1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan

Base Information

• Chemical Name: (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan
• CAS No.: 566898-20-2
• Molecular Formula: C₂₂H₃₂O₂S
• Molecular Weight: 360.561

Synonyms:(1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan

Chemical Property of (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan

There total 13 articles about (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan 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:

ethyl (E)-3-hexenoate (26553-46-8) → (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan (566898-20-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 15 percent / LiClO₄; 4,4'-thiobis(6-tert-butyl-m-cresol) / diethyl ether / 72 h / 20 °C

2.1: 74 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / 20 °C / 760 Torr

3.1: 93 percent / LiN(TMS)2 / tetrahydrofuran / 5 h / -70 - -40 °C

4.1: 72 percent / DBU / toluene / 3 h / 80 °C

5.1: 91 percent / H₂ / PtO₂ / ethanol / 4 h / 20 °C / 760 Torr

6.1: 87 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

7.1: 873 mg / BF₃*OEt₂ / CH₂Cl₂ / 16 h / -70 - 20 °C

8.1: 89 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1.5 h / 20 °C

9.1: NaN(TMS)2 / diethyl ether; toluene / 20 °C

9.2: 100 percent / diethyl ether; toluene / 14 h / 0 - 20 °C

10.1: BH₃*THF / tetrahydrofuran / 10 h / -78 - 20 °C

10.2: 70 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

11.1: 93 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

12.1: 279 mg / t-BuOK / dimethylsulfoxide / 14 h / 20 °C

With Santonox R; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 2.1: Diels-Alder reaction / 10.2: Wittig reaction;

DOI:10.1016/S0968-0896(02)00665-X

Reference yield:

(5S)-5-ethylfuran-2(5H)-one (2407-43-4,76291-90-2,92843-41-9,109668-80-6) → (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan (566898-20-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 15 percent / LiClO₄; 4,4'-thiobis(6-tert-butyl-m-cresol) / diethyl ether / 72 h / 20 °C

2.1: 74 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / 20 °C / 760 Torr

3.1: 93 percent / LiN(TMS)2 / tetrahydrofuran / 5 h / -70 - -40 °C

4.1: 72 percent / DBU / toluene / 3 h / 80 °C

5.1: 91 percent / H₂ / PtO₂ / ethanol / 4 h / 20 °C / 760 Torr

6.1: 87 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

7.1: 873 mg / BF₃*OEt₂ / CH₂Cl₂ / 16 h / -70 - 20 °C

8.1: 89 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1.5 h / 20 °C

9.1: NaN(TMS)2 / diethyl ether; toluene / 20 °C

9.2: 100 percent / diethyl ether; toluene / 14 h / 0 - 20 °C

10.1: BH₃*THF / tetrahydrofuran / 10 h / -78 - 20 °C

10.2: 70 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

11.1: 93 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

12.1: 279 mg / t-BuOK / dimethylsulfoxide / 14 h / 20 °C

With Santonox R; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Diels-Alder reaction / 9.2: Wittig reaction;

DOI:10.1016/S0968-0896(02)00665-X

Reference yield:

(3S,3aR,4S,9R,9aR)-4,9-epoxy-3-ethyl-3a,4,5,6,7,8,9,9a-octahydronaphtho[2,3-c]furan-1(3H)-one (566898-11-1) → (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan (566898-20-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 74 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / 20 °C / 760 Torr

2.1: 93 percent / LiN(TMS)2 / tetrahydrofuran / 5 h / -70 - -40 °C

3.1: 72 percent / DBU / toluene / 3 h / 80 °C

4.1: 91 percent / H₂ / PtO₂ / ethanol / 4 h / 20 °C / 760 Torr

5.1: 87 percent / DIBAL-H / diethyl ether; hexane / 1 h / -70 °C

6.1: 873 mg / BF₃*OEt₂ / CH₂Cl₂ / 16 h / -70 - 20 °C

7.1: 89 percent / 4-methylmorpholine N-oxide; molecular sieves 4 Angstroem; TPAP / CH₂Cl₂ / 1.5 h / 20 °C

8.1: NaN(TMS)2 / diethyl ether; toluene / 20 °C

8.2: 100 percent / diethyl ether; toluene / 14 h / 0 - 20 °C

9.1: BH₃*THF / tetrahydrofuran / 10 h / -78 - 20 °C

9.2: 70 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

10.1: 93 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

11.1: 279 mg / t-BuOK / dimethylsulfoxide / 14 h / 20 °C

With tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 8.2: Wittig reaction;

DOI:10.1016/S0968-0896(02)00665-X

upstream raw materials:

thiophenol

Methanesulfonic acid (1S,3S,3aR,4R,4aS,8aR,9aS)-3-ethyl-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester

ethyl (E)-3-hexenoate

(5S)-5-ethylfuran-2(5H)-one

Downstream raw materials:

(2R,6S)-2-[2-Benzenesulfonyl-1-benzoyloxy-2-((1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-1-methoxy-dodecahydro-naphtho[2,3-c]furan-4-yl)-ethyl]-6-methyl-piperidine-1-carboxylic acid tert-butyl ester

(1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylsulfonyl)methyl]naphtho[2,3-c]furan

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 566898-20-2 (1S,3S,3aS,4R,4aS,8aR,9aS)-3-ethyl-dodecahydro-1-methoxy-4-[(phenylthio)methyl]naphtho[2,3-c]furan

Send

Send

Metric Ton KG G Pound L ML

Send

Send