5-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-hexanoic acid ethyl ester

Base Information

• Chemical Name: 5-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-hexanoic acid ethyl ester
• CAS No.: 147125-14-2
• Molecular Formula: C33H56 O3 Si
• Molecular Weight: 528.88
• Mol file: 147125-14-2.mol

Synonyms:5-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-hexanoic acid ethyl ester

Chemical Property of 5-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-hexanoic acid ethyl ester

Chemical Property:

• Refractive Index: 1.504
• PSA: 35.53000
• LogP: 9.55560

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-hexanoic acid ethyl ester

There total 7 articles about 5-(4-{2-[5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene}-7a-methyl-octahydro-inden-1-yl)-hexanoic acid ethyl ester 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: 73.0%

3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (170081-45-5) + ethyl acrylate (140-88-5,9003-32-1) → ethyl 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate (147125-14-2)

Guidance literature:

With nickel dichloride; zinc; In pyridine; 1.) 60 deg C, 30 min, 2.) 20 deg C, 2.0 h;

DOI:10.1021/jo00125a051

Reference yield:

Calciferol (50-14-6) → ethyl 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate (147125-14-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) SO₂

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

3: 71 percent / I₂, PPh₃, imidazole / CH₂Cl₂ / 1.) 5 deg C, 0.5 h, 2.) room temperature, 2.0 h

4: 92.5 percent / NaHCO₃ / ethanol / 2 h / Heating

5: 73 percent / Zn, NiCl₂*6H₂O / pyridine / 1.) 60 deg C, 30 min, 2.) 20 deg C, 2.0 h

With 1H-imidazole; sodium tetrahydroborate; sulfur dioxide; iodine; sodium hydrogencarbonate; ozone; triphenylphosphine; nickel dichloride; zinc; In pyridine; ethanol; dichloromethane;

DOI:10.1021/jo00125a051

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → ethyl 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate (147125-14-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) SO₂

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

3: 71 percent / I₂, PPh₃, imidazole / CH₂Cl₂ / 1.) 5 deg C, 0.5 h, 2.) room temperature, 2.0 h

4: 92.5 percent / NaHCO₃ / ethanol / 2 h / Heating

5: 73 percent / Zn, NiCl₂*6H₂O / pyridine / 1.) 60 deg C, 30 min, 2.) 20 deg C, 2.0 h

With 1H-imidazole; sodium tetrahydroborate; sulfur dioxide; iodine; sodium hydrogencarbonate; ozone; triphenylphosphine; nickel dichloride; zinc; In pyridine; ethanol; dichloromethane;

DOI:10.1021/jo00125a051

upstream raw materials:

ethyl 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate SO2 adduct

3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene

ethyl acrylate

Calciferol

Downstream raw materials:

ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate