(S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide

Base Information

• Chemical Name: (S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide
• CAS No.: 1380210-47-8
• Molecular Formula: C₁₉H₂₈ClNO₃Si
• Molecular Weight: 381.975
• Mol file: 1380210-47-8.mol

Synonyms:(S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide

Chemical Property of (S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide

There total 3 articles about (S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide 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: 86.0%

1-tributylstannyl-3-chloropropene (155509-51-6,155197-78-7,351336-76-0) + C18H30N2O4Si (933468-32-7) → (S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide (1380210-47-8)

Guidance literature:

1-tributylstannyl-3-chloropropene; With methyllithium; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

C₁₈H₃₀N₂O₄Si; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201200064

Reference yield: 86.0%

C18H30N2O4Si (933468-32-7) + (E)-1-(tri-n-butylstannyl)-3-chloro-1-propene → (S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide (1380210-47-8)

Guidance literature:

(E)-1-(tri-n-butylstannyl)-3-chloro-1-propene; With methyllithium; trimethylaluminum; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

C₁₈H₃₀N₂O₄Si; In tetrahydrofuran; hexane; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0031-1289813

Reference yield:

N-benzoyl-O-((tert-butyl)-dimethylsilyl)-(S)-serine methyl ester (933468-31-6) → (S,E)-N-[1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl]benzamide (1380210-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylaluminum / hexane; dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: methyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

With methyllithium; trimethylaluminum; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/ejoc.201200064

upstream raw materials:

1-tributylstannyl-3-chloropropene

C₁₈H₃₀N₂O₄Si

N-benzoyl-O-((tert-butyl)-dimethylsilyl)-(S)-serine methyl ester

Downstream raw materials:

C₁₉H₃₀ClNO₃Si

C₁₉H₃₀ClNO₃Si

(4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-[(E)-3-chloroprop-1-enyl]-2-phenyl-4,5-dihydrooxazole

N-{(5S,6S)-5-[(E)-3-chloroprop-1-enyl]-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-yl}benzamide