(2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester

Base Information

• Chemical Name: (2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester
• CAS No.: 259867-07-7
• Molecular Formula: C₃₃H₄₆N₄O₉
• Molecular Weight: 642.75

Synonyms:

Chemical Property of (2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester

There total 8 articles about (2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic 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:

4-bromo-phenol (106-41-2) → (2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester (259867-07-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Na / diethyl ether

1.2: 74 percent / ZnBr₂ / CH₂Cl₂

2.1: 93 percent / K₂CO₃ / acetone / Heating

3.1: 85 percent / t-BuLi / tetrahydrofuran / -78 °C

4.1: BuLi / tetrahydrofuran / -78 - -20 °C

5.1: 56 percent / TFA / H₂O

6.1: H₂ / Pd/C / methanol

7.1: HOBt; EDCI; DIPEA / CH₂Cl₂

With n-butyllithium; hydrogen; tert.-butyl lithium; sodium; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; 1.1: Metallation / 1.2: Alkylation / 2.1: Methylation / 3.1: Carbonylation / 4.1: Addition / 5.1: Hydrolysis / 6.1: Hydrogenation / 7.1: Acylation;

DOI:10.1016/S0040-4039(99)01930-9

Reference yield:

4-Methoxy-3-(γ,γ-dimethylallyl)benzaldehyde (56074-98-7) → (2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester (259867-07-7)

Guidance literature:

Multi-step reaction with 4 steps

1: BuLi / tetrahydrofuran / -78 - -20 °C

2: 56 percent / TFA / H₂O

3: H₂ / Pd/C / methanol

4: HOBt; EDCI; DIPEA / CH₂Cl₂

With n-butyllithium; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 1: Addition / 2: Hydrolysis / 3: Hydrogenation / 4: Acylation;

DOI:10.1016/S0040-4039(99)01930-9

Reference yield:

4-bromo-2-(3-methylbut-2-en-1-yl)phenol (151071-00-0) → (2S,3R)-2-{2-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionic acid methyl ester (259867-07-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / K₂CO₃ / acetone / Heating

2: 85 percent / t-BuLi / tetrahydrofuran / -78 °C

3: BuLi / tetrahydrofuran / -78 - -20 °C

4: 56 percent / TFA / H₂O

5: H₂ / Pd/C / methanol

6: HOBt; EDCI; DIPEA / CH₂Cl₂

With n-butyllithium; hydrogen; tert.-butyl lithium; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone; 1: Methylation / 2: Carbonylation / 3: Addition / 4: Hydrolysis / 5: Hydrogenation / 6: Acylation;

DOI:10.1016/S0040-4039(99)01930-9

upstream raw materials:

Cbz-Gly-Val-Gly-OH

4-bromo-phenol

4-Methoxy-3-(γ,γ-dimethylallyl)benzaldehyde

4-bromo-2-(3-methylbut-2-en-1-yl)phenol

Downstream raw materials:

cyclic Pro-Gly-Val-Gly-Tyr(β-OH,4-methyl,3-(2-methylbutyl))-Gly-Trp

1-[2-(2-{2-{2-[2-(2-benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-acetylamino}-3-hydroxy-3-[4-methoxy-3-(3-methyl-butyl)-phenyl]-propionylamino}-acetylamino)-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester

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