(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid

Base Information

• Chemical Name: (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid
• CAS No.: 442900-69-8
• Molecular Formula: C₂₅H₂₉N₃O₅
• Molecular Weight: 451.522

Synonyms:(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid

Chemical Property of (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid

There total 3 articles about (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic 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:

Z-Trp-D-Leu-OMe (442900-68-7) → (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid (442900-69-8,253595-70-9)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃;

DOI:10.1016/S0040-4020(02)00179-5

Reference yield:

(R)-leucine methyl ester hydrochloride (5845-53-4,6322-53-8,7517-19-3) → (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid (442900-69-8,253595-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / HOBt; EDC; NEt₃ / CH₂Cl₂ / 2 h / 20 °C

2: LiOH / tetrahydrofuran; H₂O / 0 °C

With lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4020(02)00179-5

Reference yield:

N-carbobenzyloxy-L-tryptophane (7432-21-5) → (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid (442900-69-8,253595-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / HOBt; EDC; NEt₃ / CH₂Cl₂ / 2 h / 20 °C

2: LiOH / tetrahydrofuran; H₂O / 0 °C

With lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4020(02)00179-5

upstream raw materials:

Z-Trp-D-Leu-OMe

(R)-leucine methyl ester hydrochloride

N-carbobenzyloxy-L-tryptophane

Downstream raw materials:

Z-(Trp-D-Leu)2-OMe

Z-Trp-D-Leu-Trp-2-(t-butyl-diphenylsilyloxy)-ethylamide

(R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester

2-[2-amino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid [1-[2-(tert-butyl-diphenyl-silanyloxy)-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-amide

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