tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O₄-tert-butyltyrosinate

Base Information

• Chemical Name: tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O₄-tert-butyltyrosinate
• CAS No.: 129980-28-5
• Molecular Formula: C₃₁H₅₀N₂O₆
• Molecular Weight: 546.748
• Mol file: 129980-28-5.mol

Synonyms:tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O₄-tert-butyltyrosinate

Chemical Property of tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O₄-tert-butyltyrosinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O₄-tert-butyltyrosinate

There total 12 articles about tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O₄-tert-butyltyrosinate 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: 70.2%

tert-butyl (S,S,S,S)-N-(1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarbonyl)-O4-tert-butyltyrosinate → tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate (129980-28-5)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 25 - 35 ℃; under 2585.81 - 3102.97 Torr; Large scale;

DOI:10.1021/op020091f

Reference yield: 32.4%

tert-butyl (S)-N-(1-{2-tert-butoxycarbonyl-3-benzylaminopropyl}-1-cyclopentylcarbonyl)-O4-tert-butyltyrosinate → tert-butyl N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate + tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate (129980-28-5)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 30 - 40 ℃; for 8h; under 2844.39 - 3102.97 Torr; Large scale;

DOI:10.1021/op020091f

Reference yield:

2-{[Bis-((S)-1-phenyl-ethyl)-amino]-methyl}-acrylic acid tert-butyl ester (137219-70-6) → tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate (129980-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LDA / 1) 0 deg C, 1 h, 2) - 50 to - 20 deg C, 6 h

2: 1) 1-hydroxybenztriazole, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 2) H₂ / 2) 20percent Pd(OH)2/C / 1) CH₂Cl₂, 0 deg C to RT, 18 h, 2) EtOH, RT, 60 psi, 18 h

With hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; palladium dihydroxide;

DOI:10.1016/S0040-4039(00)91786-6

upstream raw materials:

tert-butyl (S)-3-(4-(tert-butoxy)phenyl)-2-aminopropanoate

(S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid

cyclopentanecarboxylic acid

tert-butyl 2-(bromomethyl)acrylate

Downstream raw materials:

(S,S,S)-N-{1-[2-carboxy-3-(N-mesyllysylamino)propyl]-1-cyclopentylcarbonyl}tyrosine