trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 80656-13-9
• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.208
• Mol file: 80656-13-9.mol

Synonyms:trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester

Chemical Property of trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester

There total 1 articles about trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl 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: 78.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (trans)-1,2-cyclopentanedicarboxylic acid (21917-20-4) → dimethyl cis-1,2-cyclopentanedicarboxylate (4841-91-2) + trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester (80656-13-9)

Guidance literature:

In diethyl ether;

DOI:10.1002/hlca.19950780512

Reference yield: 78.0%

trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester (80656-13-9) → (trans)-1,2-cyclopentanedicarboxylic acid (21917-20-4)

Guidance literature:

With sodium hydroxide; In methanol; water; Ambient temperature;

DOI:10.1021/ja00372a027

Reference yield:

trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester (80656-13-9) → (1S,2S)-Cyclopentane-1,2-dicarboxylic acid 1-benzylamide 2-(4-carbamimidoyl-benzylamide)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. NaOH / dioxane / 2 h / 20 °C

2: N-hydroxybenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; Et₃N / 20 °C / pH 8

3: aq. NaOH / dioxane

4: N-hydroxybenzotriazole; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; Et₃N / dimethylformamide / 20 °C / pH 8

5: H₂ / Pd/C / ethanol

With sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Condensation / 3: Hydrolysis / 4: Condensation / 5: Hydrogenolysis;

DOI:10.1021/jm990557t

upstream raw materials:

diazomethane

(trans)-1,2-cyclopentanedicarboxylic acid

Downstream raw materials:

(trans)-1,2-cyclopentanedicarboxylic acid

trans-methyl (1S,2S)-2-{4-[amino(benzyloxycarbonylimino)methyl]benzylaminocarbonyl}cyclopentanecarboxylate

Refernces