[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester
• CAS No.: 271600-09-0
• Molecular Formula: C₂₆H₄₁NO₄Si
• Molecular Weight: 459.701
• Mol file: 271600-09-0.mol

Synonyms:[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester

Chemical Property of [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester

There total 4 articles about [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl 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: 94.0%

benzyl N-<1-((p-methylphenyl)sulfonyl)propyl>carbamate (147169-14-0) + (1R)-2-endo-acetyl-2-exo-(trimethylsilyloxy)-1,7,7-trimethylbicyclo[2.2.1]heptane (204577-67-3) → [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester (271600-09-0)

Guidance literature:

(1R)-2-endo-acetyl-2-exo-(trimethylsilyloxy)-1,7,7-trimethylbicyclo[2.2.1]heptane; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

benzyl N-<1-((p-methylphenyl)sulfonyl)propyl>carbamate; In tetrahydrofuran; at -78 ℃; for 0.25h;

DOI:10.1002/(SICI)1521-3773(20000317)39:6<1063::AID-ANIE1063>3.0.CO;2-Y

Reference yield:

2-ethinyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (1075216-42-0) → [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester (271600-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid; mercury(II) oxide / water; acetone / 0.25 h / 60 °C

2: potassium hydride / tetrahydrofuran / 1 h / 20 °C

3: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.25 h / -78 °C

With sulfuric acid; potassium hydride; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; water; acetone; 3: Mannich reaction;

DOI:10.1021/ja026250s

Reference yield:

1-(2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-endo-2-yl)ethanone (204577-66-2) → [(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propyl]-carbamic acid benzyl ester (271600-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydride / tetrahydrofuran / 1 h / 20 °C

2: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.25 h / -78 °C

With potassium hydride; lithium diisopropyl amide; In tetrahydrofuran; hexane; 2: Mannich reaction;

DOI:10.1021/ja026250s

upstream raw materials:

benzyl N-<1-((p-methylphenyl)sulfonyl)propyl>carbamate

(1R)-2-endo-acetyl-2-exo-(trimethylsilyloxy)-1,7,7-trimethylbicyclo[2.2.1]heptane

2-ethinyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

1-(2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-endo-2-yl)ethanone

Downstream raw materials:

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

(S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-pentanoic acid

(S)-3-(N-tert-butoxycarbonylamino)pentanoic acid

[(S)-1-((S)-1-{[(S)-1-Ethyl-3-oxo-3-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-propylcarbamoyl]-methyl}-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester