E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene

Base Information

• Chemical Name: E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene
• CAS No.: 172605-71-9
• Molecular Formula: C₃₀H₅₀BrNO₃SSi
• Molecular Weight: 612.787
• Mol file: 172605-71-9.mol

Synonyms:E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene

Chemical Property of E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene

There total 5 articles about E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene 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: 88.0%

(E)-1,4-dibromobutene (821-06-7) + (+)-(5R,6S)-5-isopropyl-6-(4-methylphenylsulfonyl)amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene (172605-69-5) → E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene (172605-71-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 0.5h;

DOI:10.1016/0040-4020(95)00696-6

Reference yield:

(5S)-(+)-5-isopropenyl-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene (124603-53-8) → E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene (172605-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / hydrogen / rhodium on alumina / ethyl acetate / 48 h

2: 27 percent / 1.) selenium / CH₂Cl₂ / 1.) reflux, 3 h then 25 deg C, 16 h; 2.) 0 deg C, 6 h

3: 88 percent / 80percent sodium hydride in oil / dimethylformamide / 0.5 h / 25 °C

With selenium; hydrogen; sodium hydride; Rh/Al₂O₃; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(95)00696-6

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → E-(5R,6S)-5-isopropyl-6-amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene (172605-71-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / triethylamine / CH₂Cl₂ / 0 °C

2: 100 percent / hydrogen / rhodium on alumina / ethyl acetate / 48 h

3: 27 percent / 1.) selenium / CH₂Cl₂ / 1.) reflux, 3 h then 25 deg C, 16 h; 2.) 0 deg C, 6 h

4: 88 percent / 80percent sodium hydride in oil / dimethylformamide / 0.5 h / 25 °C

With selenium; hydrogen; sodium hydride; triethylamine; Rh/Al₂O₃; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(95)00696-6

upstream raw materials:

(E)-1,4-dibromobutene

(+)-(5R,6S)-5-isopropyl-6-(4-methylphenylsulfonyl)amino-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene

(5S)-(+)-5-isopropenyl-2-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene

triisopropylsilyl trifluoromethanesulfonate