(2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl ester

Base Information

• Chemical Name: (2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl ester
• CAS No.: 197706-58-4
• Molecular Formula: C₂₇H₃₆N₂O₆
• Molecular Weight: 484.593
• Mol file: 197706-58-4.mol

Synonyms:(2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl ester

Chemical Property of (2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl ester

There total 1 articles about (2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl 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: 76.0%

Boc-Tyr-OH (3978-80-1) + L-isoleucine benzyl ester (42406-72-4) → (2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl ester (197706-58-4)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide;

DOI:10.1021/ja9712027

Reference yield: 89.0%

(2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl ester (197706-58-4) → BOCTyrIleOH (124394-59-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; at 20 ℃; for 12h;

DOI:10.1021/ja9712027

Reference yield:

(2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoic acid benzyl ester (197706-58-4) → C34H54N8O13 (176685-67-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / H₂ / Pd/C / tetrahydrofuran; ethanol / 12 h / 20 °C

2: 61 percent / DCC, HOBt, Et₃N / dimethylformamide / 0 deg C, 30 min; 20 deg C, 16 h

3: NH₃ / methanol / 72 h / 20 °C

4: 25.7 mg / HCl / H₂O / 1 h / 20 °C

With hydrogenchloride; ammonia; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja9712027

upstream raw materials:

Boc-Tyr-OH

L-isoleucine benzyl ester

Downstream raw materials:

BOCTyrIleOH

C₃₄H₅₄N₈O₁₃

Boc-Tyr-Ile-Asn(tri-O-acetyl-β-GlcNAc-CH2)-Ala-Ser-OMe

(S)-3-{(2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-pentanoylamino}-N-[(S)-1-((S)-2-hydroxy-1-methoxycarbonyl-ethylcarbamoyl)-ethyl]-succinamic acid

Refernces