3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester

Base Information

• Chemical Name: 3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester
• CAS No.: 261786-25-8
• Molecular Formula: C₂₅H₃₂N₂O₆
• Molecular Weight: 456.539
• Mol file: 261786-25-8.mol

Synonyms:3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester

Chemical Property of 3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester

There total 8 articles about 3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic 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: 92.0%

Z-Leu-OH (2018-66-8) + 3(S)-amino-2(R,S)-hydroxy-4-phenylbutyric acid methyl ester (209174-37-8) → 3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester (261786-25-8)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm0301336

Reference yield:

2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid (209173-80-8) → 3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester (261786-25-8)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 20 °C

2: 92 percent / EDC; HOBT; NMM / dimethylformamide / 20 °C

With 4-methyl-morpholine; thionyl chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/jm0301336

Reference yield:

3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid (191849-93-1) → 3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester (261786-25-8)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. HCl / methanol / 2 h / 20 °C

2: SOCl₂ / 20 °C

3: 92 percent / EDC; HOBT; NMM / dimethylformamide / 20 °C

With 4-methyl-morpholine; hydrogenchloride; thionyl chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0301336

upstream raw materials:

Z-L-leucine hydroxysuccinimide ester

Z-Leu-OH

3(S)-amino-2(R,S)-hydroxy-4-phenylbutyric acid methyl ester

2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid

Downstream raw materials:

N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid

3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid hydrazide

N'-benzyl-3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid hydrazide

N'N'-(benzyl)(tert-butyloxycarbonylamino)-3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid hydrazide