(S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid
• CAS No.: 1026656-54-1
• Molecular Formula: C₁₉H₃₂N₂O₇
• Molecular Weight: 400.472
• Mol file: 1026656-54-1.mol

Synonyms:(S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid

Chemical Property of (S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid

There total 1 articles about (S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic 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:

(R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) → (S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid (1026656-54-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / DCC; HOBt hydrate / CH₂Cl₂ / 21 h / 0 - 20 °C

2: 98 percent / DCC; DMAP / CH₂Cl₂ / 21 h / 0 - 20 °C

3: H₂ / Pd/C / methanol / 2 h

With dmap; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jo015953+

Reference yield:

(S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid (1026656-54-1) → destruxin B (2503-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 233 mg / DCC; HOBt hydrate / CH₂Cl₂ / 25 h / 0 - 20 °C

2.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

2.2: NaNO₂; aq. HCl / 0.25 h

2.3: 65 percent / aq. NaHCO₃ / CH₂Cl₂ / 15 h / 20 °C

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo015953+

Reference yield:

(S)-1-[(R)-2-(3-tert-Butoxycarbonylamino-propionyloxy)-4-methyl-pentanoyl]-pyrrolidine-2-carboxylic acid (1026656-54-1) → homodestruxin B (110538-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / PyBrop; i-Pr₂EtN / CH₂Cl₂ / 0 - 20 °C

2.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

2.2: NaNO₂; aq. HCl / 0.25 h

2.3: 58 percent / aq. NaHCO₃ / CH₂Cl₂ / 15 h / 20 °C

With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo015953+

upstream raw materials:

(R)-2-hydroxy-4-methylpentanoic acid

Downstream raw materials:

destruxin B

homodestruxin B