(2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic acid

Base Information

• Chemical Name: (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic acid
• CAS No.: 55559-27-8
• Molecular Formula: C₂₂H₂₅N₃O₆
• Molecular Weight: 427.457
• Mol file: 55559-27-8.mol

Synonyms:(2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic acid

Chemical Property of (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic acid

There total 5 articles about (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic 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: 62.0%

benzyl N-[(1S)-4-amino-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-4-oxobutyl]carbamate (850232-63-2) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic acid (55559-27-8)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1055/s-2005-861782

Reference yield:

Cbz-L-Gln (2650-64-8) → (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic acid (55559-27-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SOCl₂ / tetrahydrofuran / 0.33 h / 35 - 40 °C

1.2: 72 percent / tetrahydrofuran / 2 h / 25 °C

2.1: aq. Et₃N / acetonitrile / 1 h / 20 °C

With thionyl chloride; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1055/s-2005-861782

Reference yield:

N2-benzyloxycarbonyl-L-glutamine-(4-nitro-phenyl ester) (7763-16-8) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (2S)-2-{[(2S)-5-amino-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoyl]amino}-3-phenylpropanoic acid (55559-27-8)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 1.66667h;

DOI:10.1016/S0040-4039(02)01840-3

upstream raw materials:

L-phenylalanine

(S)-2-Benzyloxycarbonylamino-4-carbamoyl-butyric acid 3-ethylcarbamoyl-2-hydroxy-phenyl ester

N²-benzyloxycarbonyl-L-glutamine-(4-nitro-phenyl ester)

benzyl N-[(1S)-4-amino-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-4-oxobutyl]carbamate

Downstream raw materials:

Z-Gln-Phe-Phe-OMe