(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 203053-79-6
• Molecular Formula: C₂₇H₄₃N₃O₆Si
• Molecular Weight: 533.74
• Mol file: 203053-79-6.mol

Synonyms:(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

There total 1 articles about (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl 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: 70.0%

((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoic acid (2817-13-2) + H-Pro-OTmse (108827-49-2) → (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (203053-79-6)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; for 14h; Ambient temperature;

DOI:10.1021/jo9717651

Reference yield: 93.0%

(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (203053-79-6) → (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (203053-76-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jo9717651

Reference yield:

(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (203053-79-6) → (S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid (203054-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / Bu₄NF / tetrahydrofuran / 24 h / Ambient temperature

2: 26 percent / Et₃N / toluene / 16 h / 60 °C

3: 100 percent / TFA / CH₂Cl₂ / Ambient temperature

With tetrabutyl ammonium fluoride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo9717651

upstream raw materials:

((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoic acid

H-Pro-OTmse

Downstream raw materials:

(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid

(S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid

(S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester