(3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one

Base Information

• Chemical Name: (3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one
• CAS No.: 223734-60-9
• Molecular Formula: C₃₃H₅₂O₅Si
• Molecular Weight: 556.858
• Mol file: 223734-60-9.mol

Synonyms:(3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one

Chemical Property of (3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one

There total 1 articles about (3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-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:

2-allyl-3-methoxybenzaldehyde (94956-98-6) → (3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one (223734-60-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C

2: 75 percent / PCC / CH₂Cl₂ / 15 h / 0 - 20 °C

3: BH₃; Me₂S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C

4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH₂Cl₂ / 15 h / 20 °C

5: CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; dimethylsulfide; (R)-methyloxazaborolidine; borane; ethylmagnesium bromide; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Corey reduction / 5: Pauson-Khand cyclization;

DOI:10.1021/jo0347720

Reference yield:

(3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one (223734-60-9) → treprostinil (81846-19-7)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂; K₂CO₃ / Pd/C / ethanol / 20 °C / 4654.33 Torr

2: NaBH₄; aq. NaOH / ethanol / 6 h / -10 °C

3: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C

4: 80 percent / Ph₂PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating

5: 100 percent / K₂CO₃; tetrabutylammonium bromide / acetone / 8 h / Heating

6: 83 percent / aq. KOH / methanol / 3 h / Heating

With potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; tetrabutylammomium bromide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; diphenylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; acetone;

DOI:10.1021/jo0347720

Reference yield:

(3aS,9aS)-9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a,4,9-tetrahydro-5-methoxy-1-[(3S)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octyl]-2H-benz[f]inden-2-one (223734-60-9) → (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂; K₂CO₃ / Pd/C / ethanol / 20 °C / 4654.33 Torr

2: NaBH₄; aq. NaOH / ethanol / 6 h / -10 °C

3: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C

4: 80 percent / Ph₂PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; potassium carbonate; toluene-4-sulfonic acid; diphenylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane;

DOI:10.1021/jo0347720

upstream raw materials:

2-allyl-3-methoxybenzaldehyde

Downstream raw materials:

treprostinil

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol

Refernces

• 1、 Moriarty, Robert M.,Rani, Neena,Enache, Livia A.,Rao, Munagala S.,Batra, Hitesh,Guo, Liang,Penmasta, Raju A.,Staszewski, James P.,Tuladhar, Sudersan M.,Prakash, Om,Crich, David,Hirtopeanu, Anca,Gilardi, Richard. "The Intramolecular Asymmetric Pauson-Khand Cyclization As A Novel and General Stereoselective Route to Benzindene Prostacyclins: Synthesis of UT-15 (Treprostinil)". . p. 1890 - 1902. Retrieved 2007/10/03.