(S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester
• CAS No.: 184589-18-2
• Molecular Formula: C₅₃H₆₉N₇O₁₀
• Molecular Weight: 964.172

Synonyms:

Chemical Property of (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

There total 13 articles about (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl 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:

Fmoc-Val-OH (68858-20-8) → (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (184589-18-2)

Guidance literature:

Multi-step reaction with 7 steps

1: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

2: Et₂NH / acetonitrile / 1 h / Ambient temperature

3: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

4: Et₂NH / acetonitrile / 1 h / Ambient temperature

5: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

6: Et₂NH / acetonitrile / 1 h / Ambient temperature

7: HOBt / dimethylformamide / 2.5 h / Ambient temperature

With diethyl cyanophosphonate; sodium carbonate; benzotriazol-1-ol; diethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/p19960002411

Reference yield:

Fmoc-Leu-OH (35661-60-0) → (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (184589-18-2)

Guidance literature:

Multi-step reaction with 9 steps

1: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

2: Et₂NH / acetonitrile / 1 h / Ambient temperature

3: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

4: Et₂NH / acetonitrile / 1 h / Ambient temperature

5: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

6: Et₂NH / acetonitrile / 1 h / Ambient temperature

7: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

8: Et₂NH / acetonitrile / 1 h / Ambient temperature

9: HOBt / dimethylformamide / 2.5 h / Ambient temperature

With diethyl cyanophosphonate; sodium carbonate; benzotriazol-1-ol; diethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/p19960002411

Reference yield:

Fmoc-Pro-OH (71989-31-6) → (S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester (184589-18-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 62 percent / conc. H₂SO₄ / CH₂Cl₂ / 17 h / Ambient temperature

2: Et₂NH / acetonitrile / 1 h / Ambient temperature

3: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

4: Et₂NH / acetonitrile / 1 h / Ambient temperature

5: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

6: Et₂NH / acetonitrile / 1 h / Ambient temperature

7: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

8: Et₂NH / acetonitrile / 1 h / Ambient temperature

9: diethyl phosphorocyanidate, Na₂CO₃ / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to r.t., 3 h; r.t., 2 h

10: Et₂NH / acetonitrile / 1 h / Ambient temperature

11: HOBt / dimethylformamide / 2.5 h / Ambient temperature

With diethyl cyanophosphonate; sulfuric acid; sodium carbonate; benzotriazol-1-ol; diethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/p19960002411

upstream raw materials:

(S)-1-[(S)-4-Methyl-2-((S)-3-methyl-2-{(S)-3-phenyl-2-[((S)-pyrrolidine-2-carbonyl)-amino]-propionylamino}-butyrylamino)-pentanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Fmoc-Val-OH

Fmoc-Leu-OH

Fmoc-Pro-OH

Downstream raw materials:

N-Fmoc-L-Val-L-Asn-L-Pro-L-Phe-L-Val-L-Leu-L-Pro-O-(t-Bu)

(S)-1-((S)-2-{(S)-2-[(S)-2-({(S)-1-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-carbamoyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-methyl-butyrylamino}-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

2-((3S,6S,9S,15S,18S,21S,24S)-21-Benzyl-15-isobutyl-6,18-diisopropyl-2,5,8,14,17,20,23-heptaoxo-1,4,7,13,16,19,22-heptaaza-tricyclo[22.3.0.0^9,13]heptacos-3-yl)-acetamide

(S)-1-{(S)-2-[(S)-2-((S)-2-{[(S)-1-((S)-2-Amino-3-carbamoyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-phenyl-propionylamino)-3-methyl-butyrylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid tert-butyl ester

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