(R)-2-((S)-2-{(S)-2-[(Z)-2-((S)-2-Amino-3-methyl-butyrylamino)-but-2-enoyloxy]-3-phenyl-propionyloxy}-4-methyl-pentanoylamino)-4-methyl-pentanoic acid

Base Information

• Chemical Name: (R)-2-((S)-2-{(S)-2-[(Z)-2-((S)-2-Amino-3-methyl-butyrylamino)-but-2-enoyloxy]-3-phenyl-propionyloxy}-4-methyl-pentanoylamino)-4-methyl-pentanoic acid
• CAS No.: 184034-29-5
• Molecular Formula: C₃₀H₄₅N₃O₈
• Molecular Weight: 575.703
• Mol file: 184034-29-5.mol

Synonyms:

Chemical Property of (R)-2-((S)-2-{(S)-2-[(Z)-2-((S)-2-Amino-3-methyl-butyrylamino)-but-2-enoyloxy]-3-phenyl-propionyloxy}-4-methyl-pentanoylamino)-4-methyl-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((S)-2-{(S)-2-[(Z)-2-((S)-2-Amino-3-methyl-butyrylamino)-but-2-enoyloxy]-3-phenyl-propionyloxy}-4-methyl-pentanoylamino)-4-methyl-pentanoic acid

There total 6 articles about (R)-2-((S)-2-{(S)-2-[(Z)-2-((S)-2-Amino-3-methyl-butyrylamino)-but-2-enoyloxy]-3-phenyl-propionyloxy}-4-methyl-pentanoylamino)-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:

(S)-2-hydroxyl-3,3-dimethylbutyric acid (13748-90-8,498-36-2) → (R)-2-((S)-2-{(S)-2-[(Z)-2-((S)-2-Amino-3-methyl-butyrylamino)-but-2-enoyloxy]-3-phenyl-propionyloxy}-4-methyl-pentanoylamino)-4-methyl-pentanoic acid (184034-29-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / DCC, HOBt, i-Pr₂NH / tetrahydrofuran / 0 °C

2: DMAP

3: HF / acetonitrile

4: DCC, DMAP / CH₂Cl₂

5: H₂ / Pd/C

With dmap; hydrogen fluoride; hydrogen; benzotriazol-1-ol; diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo961661a

Reference yield:

(R)-benzyl 2-amino-4-methylpentanoate hydrochloride (68838-94-8) → (R)-2-((S)-2-{(S)-2-[(Z)-2-((S)-2-Amino-3-methyl-butyrylamino)-but-2-enoyloxy]-3-phenyl-propionyloxy}-4-methyl-pentanoylamino)-4-methyl-pentanoic acid (184034-29-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / DCC, HOBt, i-Pr₂NH / tetrahydrofuran / 0 °C

2: DMAP

3: HF / acetonitrile

4: DCC, DMAP / CH₂Cl₂

5: H₂ / Pd/C

With dmap; hydrogen fluoride; hydrogen; benzotriazol-1-ol; diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo961661a

Reference yield:

Hmp-(R)-Leu-OBn (184034-25-1) → (R)-2-((S)-2-{(S)-2-[(Z)-2-((S)-2-Amino-3-methyl-butyrylamino)-but-2-enoyloxy]-3-phenyl-propionyloxy}-4-methyl-pentanoylamino)-4-methyl-pentanoic acid (184034-29-5)

Guidance literature:

Multi-step reaction with 4 steps

1: DMAP

2: HF / acetonitrile

3: DCC, DMAP / CH₂Cl₂

4: H₂ / Pd/C

With dmap; hydrogen fluoride; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In dichloromethane; acetonitrile;

DOI:10.1021/jo961661a

upstream raw materials:

Cbz-Val-(Z)-Aba-Hpp-Hmp-(R)-Leu-OBn

(S)-2-hydroxyl-3,3-dimethylbutyric acid

(R)-benzyl 2-amino-4-methylpentanoate hydrochloride

Hmp-(R)-Leu-OBn

Downstream raw materials:

Boc-Val-(Z)-Aba-Hpp-Hmp-(R)-Leu

phomalide

(3S,9S,12R,15S)-3-Benzyl-12,15-diisobutyl-9-isopropyl-6-(1-phenylselanyl-ethyl)-1,4-dioxa-7,10,13-triaza-cyclopentadecane-2,5,8,11,14-pentaone

Boc-Val-(Z)-Aba-Hpp-Hmp-(R)-Leu-OPfp