[benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: [benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester
• CAS No.: 914955-64-9
• Molecular Formula: C₁₉H₂₉NO₃
• Molecular Weight: 319.444
• Mol file: 914955-64-9.mol

Synonyms:[benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester

Chemical Property of [benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester

There total 4 articles about [benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl 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%

[1-benzyl-5-(tert-butyldiphenylsilanyloxy)-2,4-dimethylpent-2-enyl]carbamic acid tert-butyl ester (914955-63-8) → [benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester (914955-64-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol0617704

Reference yield:

[1-(4-methylbenzenesulfonyl)-2-phenylethyl]carbamic acid tert-butyl ester (914955-62-7) → [benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester (914955-64-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Cp₂ZrHCl / CH₂Cl₂ / 0.33 h / 20 °C

1.2: Me₂Zn / toluene; CH₂Cl₂ / -78 - 0 °C

1.3: 64 percent / CH₂Cl₂; toluene / 2 h / 0 °C

2.1: 47 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With Schwartz's reagent; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0617704

Reference yield:

tert-butyl carbazate (4248-19-5) → [benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester (914955-64-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 61 percent / diethyl ether / 20 °C

2.1: Cp₂ZrHCl / CH₂Cl₂ / 0.33 h / 20 °C

2.2: Me₂Zn / toluene; CH₂Cl₂ / -78 - 0 °C

2.3: 64 percent / CH₂Cl₂; toluene / 2 h / 0 °C

3.1: 47 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With Schwartz's reagent; tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ol0617704

upstream raw materials:

[1-benzyl-5-(tert-butyldiphenylsilanyloxy)-2,4-dimethylpent-2-enyl]carbamic acid tert-butyl ester

[1-(4-methylbenzenesulfonyl)-2-phenylethyl]carbamic acid tert-butyl ester

tert-butyl carbazate

phenylacetaldehyde

Downstream raw materials:

(S)-3-(tert-butoxycarbonyl)amino-4-phenyl-2-butanone

Boc-D-Phe-ψ[(E)-C(CH3)=CH]-Ala-Val-Orn(Cbz)-Leu-OMe

Boc-D-Phe-ψL[(E)-C(CH3)=CH]-Ala-Val-OMe

(S)-2-((E)-(2R,5S)-5-tert-Butoxycarbonylamino-2,4-dimethyl-6-phenyl-hex-3-enoylamino)-3-methyl-butyric acid methyl ester