(S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester
• CAS No.: 402958-28-5
• Molecular Formula: C₄₂H₆₁N₇O₈
• Molecular Weight: 791.988
• Mol file: 402958-28-5.mol

Synonyms:

Chemical Property of (S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester

There total 14 articles about (S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic 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:

L-phenylalanine tert-butyl ester hydrochloride (15100-75-1,75898-47-4) → (S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester (402958-28-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: PyBOP

1.2: i-Pr₂EtN

2.1: H₂ / Pd/C / ethyl acetate

3.1: PyBOP

3.2: i-Pr₂EtN

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/j.bmcl.2003.09.074

Reference yield:

(1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-24-1,864185-80-8) → (S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester (402958-28-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂ / Pd(OH)2/C / ethanol

2.1: DCC; HOAt

2.2: i-Pr₂EtN

3.1: aq. NaOH / ethanol

4.1: PyBOP

4.2: i-Pr₂EtN

With sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; dicyclohexyl-carbodiimide; palladium dihydroxide; In ethanol;

DOI:10.1016/j.bmcl.2003.09.074

Reference yield:

(1S,3aR,6aS)-4-Oxo-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (402958-21-8,158340-62-6) → (S)-2-(2-Hydroxy-3-{[(1S,3aR,6aS)-2-((S)-3-methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester (402958-28-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaBH₄ / ethanol

2.1: NaH / tetrahydrofuran

3.1: n-Bu₃SnH; AIBN / toluene

4.1: H₂ / Pd(OH)2/C / ethanol

5.1: DCC; HOAt

5.2: i-Pr₂EtN

6.1: aq. NaOH / ethanol

7.1: PyBOP

7.2: i-Pr₂EtN

With sodium hydroxide; sodium tetrahydroborate; 1-hydroxy-7-aza-benzotriazole; 2,2'-azobis(isobutyronitrile); benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; tri-n-butyl-tin hydride; sodium hydride; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; ethanol; toluene; 3.1: Barton deoxygenation;

DOI:10.1016/j.bmcl.2003.09.074

upstream raw materials:

2-(3-amino-2-hydroxy-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester

(1S,3aR,6aS)-2-((S)-3-Methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid

L-valyl-L-valine methyl ester

N-L-valyl-L-valine ; hydrochloride

Downstream raw materials:

(S)-2-(3-{[(1S,3aR,6aS)-2-((S)-3-Methyl-2-{(S)-3-methyl-2-[(pyrazine-2-carbonyl)-amino]-butyrylamino}-butyryl)-octahydro-cyclopenta[c]pyrrole-1-carbonyl]-amino}-2-oxo-hexanoylamino)-3-phenyl-propionic acid tert-butyl ester

Refernces