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

Base Information

• Chemical Name: [N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid methyl ester
• CAS No.: 864360-87-2
• Molecular Formula: C₂₅H₄₁NO₅Si
• Molecular Weight: 463.69
• Mol file: 864360-87-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about [N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid methyl 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: 90.0%

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) + [(Z)-1-bromomethyl-4-tert-butoxybut-1-enyl]dimethyl(phenyl)silane (583041-48-9) → [N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid methyl ester (864360-87-2)

Guidance literature:

N-(tert-butoxycarbonyl)glycine methyl ester; With potassium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

[(Z)-1-bromomethyl-4-tert-butoxybut-1-enyl]dimethyl(phenyl)silane; In tetrahydrofuran; at 0 - 20 ℃; for 17h;

DOI:10.1039/b506198a

Reference yield: 99.0%

[N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid methyl ester (864360-87-2) → [N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid (864360-93-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 23h;

DOI:10.1039/b506198a

Reference yield:

[N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid methyl ester (864360-87-2) → [2-(2-tert-butoxy-ethyl)-3-(dimethyl-phenyl-silanyl)-1-formyl-but-3-enyl]-carbamic acid tert-butyl ester (864360-94-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / aq. NaOH / tetrahydrofuran / 23 h / 20 °C

2: 72 percent / DCC; DMAP / CH₂Cl₂ / 14 h / -30 - 20 °C

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

4: 70 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

5: Dess-Martin periodinane / CH₂Cl₂ / 14 h / 20 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; 18-crown-6 ether; potassium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; 3: aza-<2,3>-Wittig sigmatropic rearrangement / 5: Dess-Martin oxidation;

DOI:10.1039/b506198a

upstream raw materials:

N-(tert-butoxycarbonyl)glycine methyl ester

[(Z)-1-bromomethyl-4-tert-butoxybut-1-enyl]dimethyl(phenyl)silane

Downstream raw materials:

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

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