(E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid

Base Information

• Chemical Name: (E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid
• CAS No.: 178940-74-4
• Molecular Formula: C₁₆H₃₀O₃Si
• Molecular Weight: 298.498
• Mol file: 178940-74-4.mol

Synonyms:(E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid

Chemical Property of (E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid

There total 10 articles about (E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid 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: 54.0%

(E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid allyl ester (178940-62-0) → (E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid (178940-74-4)

Guidance literature:

With lithium dimethylcuprate; In diethyl ether; 1.) -20 deg C, 1 h, 2.) -20 to 0 deg C;

DOI:10.1039/p19960001171

Reference yield:

trans-3-(Trimethylsilyl)-2-propensaeure (58207-98-0) → (E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid (178940-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1: (COCl)2 / CH₂Cl₂ / 2 h / Ambient temperature

2: BuLi / tetrahydrofuran; hexane / 1.) -20 deg C, 20 min, 2.) -78 deg C, 0.5 h

4: 52 percent / LDA / hexane; tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 1 h

5: 54 percent / Me₂CuLi / diethyl ether / 1.) -20 deg C, 1 h, 2.) -20 to 0 deg C

With n-butyllithium; oxalyl dichloride; lithium dimethylcuprate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1039/p19960001171

Reference yield:

trans-3-(Trimethylsilyl)-2-propenoylchlorid (88946-48-9) → (E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid (178940-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1: BuLi / tetrahydrofuran; hexane / 1.) -20 deg C, 20 min, 2.) -78 deg C, 0.5 h

3: 52 percent / LDA / hexane; tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 1 h

4: 54 percent / Me₂CuLi / diethyl ether / 1.) -20 deg C, 1 h, 2.) -20 to 0 deg C

With n-butyllithium; lithium dimethylcuprate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1039/p19960001171

upstream raw materials:

(E)-(2S,3R)-5-Cyclohexyl-3-hydroxy-2-((R)-1-trimethylsilanyl-ethyl)-pent-4-enoic acid allyl ester

trans-3-(Trimethylsilyl)-2-propensaeure

(E)-3-cyclohexylpropenal

trans-3-(Trimethylsilyl)-2-propenoylchlorid