[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

Base Information

• Chemical Name: [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester
• CAS No.: 864360-88-3
• Molecular Formula: C₄₀H₆₁NO₅Si
• Molecular Weight: 664.014
• Mol file: 864360-88-3.mol

Synonyms:[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

Chemical Property of [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester

There total 5 articles about [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol 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: 47.0%

[N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)pent-2-enyl]amino]acetic acid [1R,2S,5R]-8-phenylmenthol ester (864360-86-1) → 2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester + [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester (864360-88-3)

Guidance literature:

With 18-crown-6 ether; potassium hydride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1039/b506198a

Reference yield:

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) → [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester (864360-88-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: KH / tetrahydrofuran / 1 h / 0 °C

1.2: 90 percent / tetrahydrofuran / 17 h / 0 - 20 °C

2.1: 99 percent / aq. NaOH / tetrahydrofuran / 23 h / 20 °C

3.1: 72 percent / DCC; DMAP / CH₂Cl₂ / 14 h / -30 - 20 °C

4.1: 47 percent / 18-C-6; KH / tetrahydrofuran / 3 h / 20 °C

With dmap; sodium hydroxide; 18-crown-6 ether; potassium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 4.1: aza-<2,3>-Wittig sigmatropic rearrangement;

DOI:10.1039/b506198a

Reference yield:

[N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid (864360-93-0) → [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid [1R,2S,5R]-8-phenylmenthol ester (864360-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / DCC; DMAP / CH₂Cl₂ / 14 h / -30 - 20 °C

2: 47 percent / 18-C-6; KH / tetrahydrofuran / 3 h / 20 °C

With dmap; 18-crown-6 ether; potassium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 2: aza-<2,3>-Wittig sigmatropic rearrangement;

DOI:10.1039/b506198a

upstream raw materials:

[N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)pent-2-enyl]amino]acetic acid [1R,2S,5R]-8-phenylmenthol ester

[N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid

[N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid methyl ester

N-(tert-butoxycarbonyl)glycine methyl ester

Downstream raw materials:

[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid

[2-(2-tert-butoxy-ethyl)-3-(dimethyl-phenyl-silanyl)-1-formyl-but-3-enyl]-carbamic acid tert-butyl ester

[2S,3R]-[2-(2-tert-butoxyethyl)-3-(dimethylphenylsilanyl)-1-hydroxymethylbut-3-enyl]carbamic acid tert-butyl ester