[3aS-(3aa,4a,5b,6aa)]-4-[[[(tert-Butyl)dimethylsilyl]oxy]methyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexahydro-2(1H)-pentalenone

Base Information

• Chemical Name: [3aS-(3aa,4a,5b,6aa)]-4-[[[(tert-Butyl)dimethylsilyl]oxy]methyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexahydro-2(1H)-pentalenone
• CAS No.: 112168-22-6
• Molecular Formula: C20H36O4
• Molecular Weight: 368.589
• Mol file: 112168-22-6.mol

Synonyms:ILTBS(iloprost lactone);

Chemical Property of [3aS-(3aa,4a,5b,6aa)]-4-[[[(tert-Butyl)dimethylsilyl]oxy]methyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexahydro-2(1H)-pentalenone

Chemical Property:

• Appearance/Colour: white
• Boiling Point: 429.494 °C at 760 mmHg
• Flash Point: 177.422 °C
• PSA: 44.76000
• Density: 1.03 g/cm³
• LogP: 4.53520
• Storage Temp.: 2-8°C

Purity/Quality:

99.5% ^*data from raw suppliers

(3AS,4S,5R,6aR)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydropentalen-2(1H)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [3aS-(3aa,4a,5b,6aa)]-4-[[[(tert-Butyl)dimethylsilyl]oxy]methyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexahydro-2(1H)-pentalenone

There total 16 articles about [3aS-(3aa,4a,5b,6aa)]-4-[[[(tert-Butyl)dimethylsilyl]oxy]methyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexahydro-2(1H)-pentalenone 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: 81.0%

[(1S,2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methoxycarbonylmethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester (112168-21-5) → [3aS-(3aα,4α,5β,6aα)]-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2(1H)-pentalenone (112168-22-6)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; water; dimethyl sulfoxide; at 175 ℃;

DOI:10.1039/c39870000267

Reference yield: 23.0%

[5R-(5α,6β,6aα)]-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4,5,6,6a-tetrahydro-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2(1H)-pentalenone (81845-46-7) → [3aS-(3aα,4α,5β,6aα)]-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2(1H)-pentalenone (112168-22-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; triethylamine; In toluene; at 20 ℃; under 2625.26 Torr; Large scale;

Reference yield:

C20H24N2O6S4 → [3aS-(3aα,4α,5β,6aα)]-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]hexahydro-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2(1H)-pentalenone (112168-22-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 16 percent / Et₃N / CH₂Cl₂ / 0 °C

2: 72 percent / HCl / dioxane / 60 °C

3: 94 percent / methanol; tetrahydrofuran / -60 - 10 °C

4: dicyclohexylcarbodiimide, hydroxybenzotriazole / 1.) THF 2.) Et₃N

5: 57 percent / lithium diisopropylamine / tetrahydrofuran; hexamethylphosphoric acid triamide / -55 °C

6: 87 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

7: imidazole, pyridinum toluene-p-sulphonate / 1.) dimethylformamide 2.) Ch₂Cl₂

8: 84 percent / NaIO₄, KMnO₄, Na₂CO₃, CH₂N₂ / dioxane; H₂O; diethyl ether

9: 81 percent / NaH, hexamethylphosphoramide / dimethylsulfoxide; hexamethylphosphoric acid triamide; H₂O / 175 °C

With diazomethane; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium permanganate; sodium periodate; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; sodium carbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1039/c39870000267

upstream raw materials:

[(1S,2S,3R,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methoxycarbonylmethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

3,4-dihydro-2H-pyran

methyl (1S,6S,7R)-8-oxobicyclo[4.3.0]non-3-ene-7-carboxylate

tert-butyldimethylsilyl chloride

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