(R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid

Base Information

• Chemical Name: (R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid
• CAS No.: 215872-24-5
• Molecular Formula: C₂₆H₃₃N₃O₆
• Molecular Weight: 483.565
• Mol file: 215872-24-5.mol

Synonyms:(R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid

Chemical Property of (R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid

There total 1 articles about (R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid 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:

Fmoc-Val-OH (68858-20-8) + N-(9-fluorenylmethoxycarbonyl)-D-alanine (35661-38-2,35661-39-3,79990-15-1,136132-75-7) + N-ac-(O-benzyl)tyrosine (73535-46-3) → (R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid (215872-24-5)

Guidance literature:

Multistep reaction;

DOI:10.1021/jm9802766

Reference yield:

(R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid (215872-24-5) → Phosphoric acid mono-(4-{(S)-2-acetylamino-2-[(S)-1-((R)-1-dibutylcarbamoyl-ethylcarbamoyl)-2-methyl-propylcarbamoyl]-ethyl}-phenyl) ester

Guidance literature:

Multi-step reaction with 3 steps

1: EDCI, HOBt, NMM / tetrahydrofuran / 6 h

2: H₂ / 20percent Pd/C / methanol / 2585.7 - 2844.3 Torr

3: 1.) 1H-tetrazole, di-tert-butyl diethylphosphoramidite, 2.) 70percent aq. tert-butyl hydroperoxide, 3.) 95percent aq. TFA

With 4-methyl-morpholine; 1H-tetrazole; tert.-butylhydroperoxide; hydrogen; di-tert-butyl N,N-diethylphosphoramidite; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jm9802766

Reference yield:

(R)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid (215872-24-5) → (S)-2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-N-((R)-1-dioctylcarbamoyl-ethyl)-3-methyl-butyramide

Guidance literature:

Multi-step reaction with 2 steps

1: HATU, HOAt, NMM / methanol / 6 h

2: H₂ / 20percent Pd/C / methanol / 2585.7 - 2844.3 Torr

With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In methanol;

DOI:10.1021/jm9802766

upstream raw materials:

Fmoc-Val-OH

N-(9-fluorenylmethoxycarbonyl)-D-alanine

N-ac-(O-benzyl)tyrosine

Downstream raw materials:

(S)-2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-N-((R)-1-dihexylcarbamoyl-ethyl)-3-methyl-butyramide