(S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate

Base Information

• Chemical Name: (S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate
• CAS No.: 1207472-62-5
• Molecular Formula: C₂₇H₄₁NO₄
• Molecular Weight: 443.627
• Mol file: 1207472-62-5.mol

Synonyms:(S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate

Chemical Property of (S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate

There total 12 articles about (S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate 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%

(-)-menthol (2216-51-5) + [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-methyl-5-phenyl-2-pentenoic acid (356788-71-1) → (S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate (1207472-62-5)

Guidance literature:

(-)-menthol; [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-methyl-5-phenyl-2-pentenoic acid; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 18h;

With oxalic acid; In dichloromethane; for 0.5h;

DOI:10.1055/s-0041-1737139

Reference yield: 78.0%

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(triphenylphosphoranylidene)propanoate (1082984-76-6) + Boc-L-phenylalaninal (72155-45-4) → (S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate (1207472-62-5)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 8.25h;

DOI:10.1002/chem.201700874

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → (S,E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-2-enoate (1207472-62-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / dichloromethane / -78 - 20 °C

2.1: sodium hydroxide / 1,4-dioxane / 2 h / 80 °C

2.2: pH 2

3.1: dmap; dicyclohexyl-carbodiimide / diethyl ether / 0 - 20 °C

With dmap; potassium tert-butylate; dicyclohexyl-carbodiimide; sodium hydroxide; In 1,4-dioxane; diethyl ether; dichloromethane; 1.1: Wittig reaction;

DOI:10.1002/ejoc.200900999

upstream raw materials:

(-)-menthol

[L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-methyl-5-phenyl-2-pentenoic acid

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Boc-L-phenylalaninal

Downstream raw materials:

methyl (2S,4R)-2-methyl-4-[({2-[(3R)-4-methyl-3-{methyl[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-phenylpentanoate

(2S,4R)-4-[((R)-2-{3-[methyl-(N-methyl-(R)-pipecolyl-(S)-isoleucyl)-amino]-4-methyl-pentyl}-thiazole-4-carbonyl)-amino]-2-methyl-5-phenyl-pentanoic acid trifluoroacetic acid salt

methyl (2S,4R)-4-[((R)-2-{3-[(N-benzyloxycarbonyl-(R)-pipecolyl-(S)-isoleucyl)methylamino]-4-methylpentyl}thiazole-4-carbonyl)amino]-2-methyl-5-phenylpentanoate