ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate

Base Information

• Chemical Name: ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate
• CAS No.: 140480-24-6
• Molecular Formula: C₂₁H₂₈N₄O₆
• Molecular Weight: 432.477
• Mol file: 140480-24-6.mol

Synonyms:ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate

Chemical Property of ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate

There total 3 articles about ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate 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:

(R)-4-{(2S,3R)-2-Benzyloxycarbonylamino-3-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-3-hydroxy-propionylamino}-pentanoic acid ethyl ester → ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate (140480-24-6)

Guidance literature:

With 3-mercaptopropionic acid; In tetrahydrofuran; for 1h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)90783-5

Reference yield:

Nα-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidine (101485-34-1) → ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate (140480-24-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / NaHCO₃ / methanol; H₂O / 16 h / Ambient temperature

2: 4-methylmorpholine, EDCI, HOBT*H₂O / dimethylformamide / 14 h / Ambient temperature

3: 3-mercaptopropionic acid / tetrahydrofuran / 1 h / Ambient temperature

With 4-methyl-morpholine; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-mercaptopropionic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90783-5

Reference yield:

Nα-(benzyloxycarbonyl)-Nim-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine (140480-22-4) → ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidyl>amino>pentanoate (140480-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methylmorpholine, EDCI, HOBT*H₂O / dimethylformamide / 14 h / Ambient temperature

2: 3-mercaptopropionic acid / tetrahydrofuran / 1 h / Ambient temperature

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-mercaptopropionic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90783-5

upstream raw materials:

N^α-(benzyloxycarbonyl)-erythro-β-hydroxy-L-histidine

N^α-(benzyloxycarbonyl)-N^im-(2,4-dinitrophenyl)-erythro-β-hydroxy-L-histidine

Downstream raw materials:

ethyl (S)-4-<α-(benzyloxycarbonyl)-erythro-β-tert-butoxy-L-histidyl>amino>pentanoate

(S)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridyl>carbonyl>-erythro-β-tert-butoxy-L-histidyl>amino>pentanoic acid

ethyl (S)-4-<α-<<6-<amino>ethyl>-N-<(o-nitrophenyl)thio>amino>methyl>-4-methoxy-2-pyridyl>carbonyl>-erythro-β-tert-butoxy-L-histidyl>amino>pentanoate