(S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester

Base Information

• Chemical Name: (S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester
• CAS No.: 143677-70-7
• Molecular Formula: C₃₀H₅₃NO₄Si
• Molecular Weight: 519.841
• Mol file: 143677-70-7.mol

Synonyms:(S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester

Chemical Property of (S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester

There total 7 articles about (S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl 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: 50.0%

(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-al (118635-66-8) + Dimethyl-[(1S,2R)-1-methyl-2-phenyl-2-((E)-1-trimethylsilanyloxy-oct-1-enyloxy)-ethyl]-amine (143730-56-7) → (S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester (143677-70-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 1.5h;

DOI:10.1016/0040-4020(92)80006-2

Reference yield:

(-)-N-methylephedrine (552-79-4) → (S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester (143677-70-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 2) 1N NaOH / 1) CH₂Cl₂, rt, 8 h, 2) rt, 8 h

2: 1) LDA / 1) THF/hexane, -78 deg C, 1 h, 2) a) -78 deg C, 30 min, b) -78 deg C to rt, 1 h

3: 50 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

With sodium hydroxide; titanium tetrachloride; lithium diisopropyl amide; In dichloromethane;

DOI:10.1016/0040-4020(92)80006-2

Reference yield:

3-tert-butyldimethylsilyloxy-1-propanol (73842-99-6) → (S)-2-[(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-2-enyl]-octanoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester (143677-70-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) ClCO-COCl, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -70 deg C, 2) -30 to 0 deg C

2: 80 percent / benzene / 5 h / Heating

3: 50 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

With oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In dichloromethane; benzene;

DOI:10.1016/0040-4020(92)80006-2

upstream raw materials:

(E)-5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-al

Dimethyl-[(1S,2R)-1-methyl-2-phenyl-2-((E)-1-trimethylsilanyloxy-oct-1-enyloxy)-ethyl]-amine

(-)-N-methylephedrine

3-tert-butyldimethylsilyloxy-1-propanol