(1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Base Information

• Chemical Name: (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester
• CAS No.: 667468-11-3
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384
• Mol file: 667468-11-3.mol

Synonyms:(1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Chemical Property of (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

There total 1 articles about (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-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:

(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) → (1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (667468-11-3) + (1S,3aR,4S,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Guidance literature:

With sodium tetrahydroborate; In ethanol;

DOI:10.1016/S0960-894X(03)00753-4 DOI:10.1016/j.bmcl.2003.09.074

Reference yield: 90.0%

(1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (667468-11-3) → (1S,3aR,4S,6aS)-4-Fluoro-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane;

DOI:10.1016/S0960-894X(03)00753-4

Reference yield:

(1S,3aR,4R,6aS)-4-Hydroxy-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester (667468-11-3) → (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

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran

2.1: n-Bu₃SnH; AIBN / toluene

3.1: H₂ / Pd(OH)2/C / ethanol

4.1: DCC; HOAt

4.2: i-Pr₂EtN

5.1: aq. NaOH / ethanol

6.1: PyBOP

6.2: i-Pr₂EtN

7.1: Dess-Martin periodinane / tetrahydrofuran

8.1: TFA / CH₂Cl₂

With sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; 2,2'-azobis(isobutyronitrile); benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; tri-n-butyl-tin hydride; sodium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; toluene; 2.1: Barton deoxygenation / 7.1: Dess-Martin oxidation;

DOI:10.1016/j.bmcl.2003.09.074

upstream raw materials:

(1S,3aR,6aS)-4-Oxo-hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

Downstream raw materials:

(1S,3aR,6aS)-ethyl octahydrocyclopenta[c]pyrrole-1-carboxylate

(1S,3aR,6aS)-Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-benzyl ester 1-ethyl ester

(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

Refernces

• 1、 Yip, Yvonne,Victor, Frantz,Lamar, Jason,Johnson, Robert,Wang, Q. May,Barket, Donna,Glass, John,Jin, Ling,Liu, Lifei,Venable, Daryl,Wakulchik, Mark,Xie, Congping,Heinz, Beverly,Villarreal, Elcira,Colacino, Joe,Yumibe, Nathan,Tebbe, Mark,Munroe, John,Chen, Shu-Hui. "Discovery of a novel bicycloproline P2 bearing peptidyl α-ketoamide LY514962 as HCV protease inhibitor". . p. 251 - 256. Retrieved 2007/10/03.