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

Base Information

• Chemical Name: (S)-2-((E)-(2R,5S)-5-tert-Butoxycarbonylamino-2,4-dimethyl-6-phenyl-hex-3-enoylamino)-3-methyl-butyric acid methyl ester
• CAS No.: 914955-65-0
• Molecular Formula: C₂₅H₃₈N₂O₅
• Molecular Weight: 446.587
• Mol file: 914955-65-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (S)-2-((E)-(2R,5S)-5-tert-Butoxycarbonylamino-2,4-dimethyl-6-phenyl-hex-3-enoylamino)-3-methyl-butyric 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:

[benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester (914955-64-9) + L-valine methylester hydrochloride (6306-52-1) → Boc-D-Phe-ψL[(E)-C(CH3)=CH]-Ala-Val-OMe (914955-66-1) + (S)-2-((E)-(2R,5S)-5-tert-Butoxycarbonylamino-2,4-dimethyl-6-phenyl-hex-3-enoylamino)-3-methyl-butyric acid methyl ester (914955-65-0)

Guidance literature:

[benzyl-5-hydroxyl-2,4R-dimethylpent-2-enyl]carbamic acid tert-butyl ester; With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 3h;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; at 0 - 20 ℃; for 5h;

L-valine methylester hydrochloride; With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In chloroform; at 20 ℃; for 36h;

DOI:10.1021/ol0617704

Reference yield:

[1-(4-methylbenzenesulfonyl)-2-phenylethyl]carbamic acid tert-butyl ester (914955-62-7) → (S)-2-((E)-(2R,5S)-5-tert-Butoxycarbonylamino-2,4-dimethyl-6-phenyl-hex-3-enoylamino)-3-methyl-butyric acid methyl ester (914955-65-0)

Guidance literature:

Multi-step reaction with 3 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

3.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 - 20 °C

3.2: 2-methyl-2-butene; NaClO₂; NaH₂PO₄*H₂O / tetrahydrofuran; H₂O / 5 h / 0 - 20 °C

3.3: HOBt; EDC; triethylamine / CHCl₃ / 36 h / 20 °C

With Schwartz's reagent; tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0617704

Reference yield:

[1-benzyl-5-(tert-butyldiphenylsilanyloxy)-2,4-dimethylpent-2-enyl]carbamic acid tert-butyl ester (914955-63-8) → (S)-2-((E)-(2R,5S)-5-tert-Butoxycarbonylamino-2,4-dimethyl-6-phenyl-hex-3-enoylamino)-3-methyl-butyric acid methyl ester (914955-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 47 percent / TBAF / tetrahydrofuran / 0 - 20 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 - 20 °C

2.2: 2-methyl-2-butene; NaClO₂; NaH₂PO₄*H₂O / tetrahydrofuran; H₂O / 5 h / 0 - 20 °C

2.3: HOBt; EDC; triethylamine / CHCl₃ / 36 h / 20 °C

With tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0617704

upstream raw materials:

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

L-valine methylester hydrochloride

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

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

Downstream raw materials:

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