(S)-2-((1R,3aS,7aR,E)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)propan-1-ol

Base Information

• Chemical Name: (S)-2-((1R,3aS,7aR,E)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)propan-1-ol
• CAS No.: 128387-35-9
• Molecular Formula: C34H62O3Si2
• Molecular Weight: 575.035
• Mol file: 128387-35-9.mol

Synonyms:(S)-2-((1R,3aS,7aR,E)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)propan-1-ol;G4/(S)-2-((1R,3aS,7aR,E)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)propan-1-ol

Chemical Property of (S)-2-((1R,3aS,7aR,E)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)propan-1-ol

Chemical Property:

• Boiling Point: 572.7±50.0 °C(Predicted)
• PKA: 14.97±0.10(Predicted)
• PSA: 38.69000
• Density: 0.96±0.1 g/cm3(Predicted)
• LogP: 9.81480
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Dichloromethane

Purity/Quality:

99% ^*data from raw suppliers

(βS,1R,3aS,4E,7aR)-4-[(2E)-2-[(3S,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethylidene]octahydro-β,7a-dimethyl-1H-indene-1-ethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (βS,1R,3aS,4E,7aR)-4-[(2E)-2-[(3S,5R)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethylidene]octahydro-β,7a-dimethyl-1H-indene-1-ethanol is an intermediate in synthesizing ZK 159222 (Z485800), a vitamin D receptor antagonist. It is a derivative of Vitamin D3 (V676045).

Technology Process of (S)-2-((1R,3aS,7aR,E)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)propan-1-ol

There total 2 articles about (S)-2-((1R,3aS,7aR,E)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)propan-1-ol 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: 47.0%

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene SO2 adduct → (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (128387-35-9)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 5h; Heating;

DOI:10.1021/jo00125a051

Reference yield:

(6S)- and (6R)-SO2 adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10(19),22(E)-tetraene (170081-46-6) → (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (128387-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -10 deg C, 45 min, 2.) room temperature, 2 h

2: 47 percent / NaHCO₃ / aq. ethanol / 5 h / Heating

With sodium tetrahydroborate; sodium hydrogencarbonate; ozone; In ethanol;

DOI:10.1021/jo00125a051

Reference yield: 95.0%

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (128387-35-9) → (5E,7E)-(1S,3R,20S)-1,3-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-20-methyl-9,10-secopregna-5,7,10(19)-trien-21-al (112828-13-4)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; Molecular sieve;

DOI:10.1016/j.tetlet.2009.06.049

upstream raw materials:

(6S)- and (6R)-SO₂ adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene

Downstream raw materials:

((S)-2-{(R)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propoxy)-acetic acid tert-butyl ester

23-Oxa-calcitriol

1-((S)-2-{(R)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propoxy)-2-methyl-propan-2-ol

1-((S)-2-{(R)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propoxy)-2-methyl-propan-2-ol