1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-carboxylic acid

Base Information

• Chemical Name: 1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-carboxylic acid
• CAS No.: 88315-64-4
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.181
• Mol file: 88315-64-4.mol

Synonyms:(1S,2R)-cis-2-methoxycarbonyl-cyclopentane-1-carboxylic acid

Chemical Property of 1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-carboxylic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-carboxylic acid

There total 12 articles about 1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-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: 100.0%

methanol (67-56-1) + cyclopentane-cis-1,2-dicarboxylic acid anhydride (35878-28-5,743438-34-8) → (1S,2R)-cis-2-methoxycarbonyl-cyclopentane-1-carboxylic acid (88315-64-4)

Guidance literature:

With C₂₈H₂₇F₆N₃O₃S; In tetrahydrofuran; at 25 ℃; for 48h; Inert atmosphere;

DOI:10.1039/c9cc03895g

Reference yield: 100.0%

methanol (67-56-1) + 1-cyclopentene-1,2-dicarboxylic anhydride (3205-94-5) → (1S,2R)-cis-2-methoxycarbonyl-cyclopentane-1-carboxylic acid (88315-64-4)

Guidance literature:

With quinine; In tetrachloromethane; toluene; at -55 ℃; for 36h;

Reference yield: 75.0%

1-methyl hydrogen (1S*,2R*)-1,2-cyclopentanedicarboxylate → (1,2-trans)-2-(methoxycarbonyl)cyclopentanecarboxylic acid (88315-64-4,88335-90-4,92541-43-0,98168-34-4,111138-44-4,111138-48-8,111138-68-2,124916-60-5)

Guidance literature:

With lithium diisopropyl amide; at -78 ℃; for 4h; Inert atmosphere;

upstream raw materials:

methanol

cyclopentane-cis-1,2-dicarboxylic acid anhydride

1-cyclopentene-1,2-dicarboxylic anhydride

dimethyl cis-1,2-cyclopentanedicarboxylate

Downstream raw materials:

(1S,2S)-Cyclopentane-1,2-dicarbonyl dichloride

(1S,2S)-cyclopentane-1,2-dicarboxylic acid 1-[(2'-hydroxy-1'-(S)-tert-butylethyl)-amide]-2-[(2''-hydroxy-1''-(S)-phenylethyl)-amide]

(1S,2S)-cyclopentane-1,2-dicarboxylic acid 1-[(2'-hydroxy-1'-(S)-tert-butylethyl)-amide]-2-[(2''-hydroxy-1''-(R)-phenylethyl)-amide]

(trans)-1,2-cyclopentanedicarboxylic acid

Refernces

• 1、 Zhang, Fan,Wen, Xiaoan,Xu, Qing-Long,Sun, Hongbin. "Asymmetric synthesis of 3,4-disubstituted proline derivatives: Application in synthesis of hepatitis C virus protease inhibitor telaprevir". . p. 8101 - 8109. Retrieved 2015/02/02.
• 2、 -. "NOVEL HEPATITIS C VIRUS INHIBITORS". Page/Page column 61. . Retrieved 2013/07/05.