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

Base Information

• Chemical Name: (5R)-ethyl 5-((1R,3aS,7aR)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethyl)-7a-Methyloctahydro-1H-inden-1-yl)hexanoate
• CAS No.: 169900-32-7
• Molecular Formula: C39H70O4Si2
• Molecular Weight: 659.153
• Mol file: 169900-32-7.mol

Synonyms:5-(4-{2-[3,5-BIS-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-2-METHYLENE-CYCLOHEXYLIDENE]-ETHYLIDENE}-7A-METHYL-OCTAHYDRO-INDEN-1-YL)-HEXANOIC ACID ETHYL ESTER;ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate;(5R)-ethyl 5-((1R,3aS,7aR)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-1-yl)hexanoate;(R)-5-{(1R,3aS,7aR)-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}-hexanoic acid ethyl ester;ETHYL (5R)-5-[(1R,4E,7AR)-4-{2-[(1E,3S,5R)-3,5-BIS[(TERT-BUTYLDIMETHYLSILYL)OXY]-2-METHYLIDENECYCLOHEXYLIDENE]ETHYLIDENE}-7A-METHYL-OCTAHYDRO-1H-INDEN-1-YL]HEXANOATE;

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 619.064°C at 760 mmHg
• Flash Point: 272.565°C
• PSA: 44.76000
• Density: 0.971g/cm³
• LogP: 11.55590

Purity/Quality:

99% ^*data from raw suppliers

(5R)-ethyl5-((1R,3aS,7aR)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-1-yl)hexanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 7 articles about (5R)-ethyl 5-((1R,3aS,7aR)-4-((E)-2-((3S,5R)-3,5-bis(tert-butyldiMethylsilyloxy)-2-Methylenecyclohexylidene)ethyl)-7a-Methyloctahydro-1H-inden-1-yl)hexanoate 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: 86.5%

ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate SO2 adduct → ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate (169900-32-7)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 2.25h; Heating;

DOI:10.1021/jo00125a051

Reference yield: 77.0%

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (147125-06-2) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate (169900-32-7)

Guidance literature:

With iodine; nickel dichloride; zinc; In pyridine; for 0.75h; Ambient temperature;

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) → ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate (169900-32-7)

Guidance literature:

Multi-step reaction with 4 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

3: 87 percent / imidazole, PPh₃, I₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 77 percent / Zn, NiCl₂*6H₂O, I₂ / pyridine / 0.75 h / Ambient temperature

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

DOI:10.1021/jo00125a051

upstream raw materials:

tert-butyldimethylsilyl chloride

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

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene

ethyl acrylate

Downstream raw materials:

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

(1S),3(R)-9,10-secocholesta-5(E),7(E),10⁽¹⁹⁾-triene-1,3,25-triol

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

calcitriol