(1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

Base Information

• Chemical Name: (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid
• CAS No.: 115694-82-1
• Molecular Formula: C₈H₁₀O₅
• Molecular Weight: 186.164
• Mol file: 115694-82-1.mol

Synonyms:(1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

Chemical Property of (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

There total 3 articles about (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic 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: 49.0%

(+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) (6453-07-2,28269-02-5,28269-03-6,35079-19-7,74500-50-8,115794-30-4) → trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (35079-19-7) + (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (115694-82-1)

Guidance literature:

With phosphate buffer; pig liver esterase; In water; for 1h; pH=7.0;

DOI:10.1002/anie.200460203

Reference yield:

(+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) (6453-07-2,28269-02-5,28269-03-6,35079-19-7,74500-50-8,115794-30-4) → (1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (1445591-99-0) + (+)-(1S,2S)-dimethyl-4-oxocyclopentane 1,2-dicarboxylate (115794-30-4) + trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (35079-19-7) + (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (115694-82-1)

Guidance literature:

With Aminoacylase from Aspergillus sp; In aq. phosphate buffer; at 15 - 20 ℃; for 16h; pH=7; Reagent/catalyst; Temperature; Resolution of racemate; Enzymatic reaction;

Reference yield:

racemic trans-cyclopentanone-3,4-dicarboxylic acid (1703-61-3,3128-17-4,3128-18-5,67885-97-6) → trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (35079-19-7) + (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (115694-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / toluene / 30 - 70 °C / Large scale

2: Aminoacylase from Aspergillus sp. / toluene; aq. phosphate buffer / 20 °C / pH 7 / Resolution of racemate; Enzymatic reaction

With sulfuric acid; In aq. phosphate buffer; toluene;

upstream raw materials:

(+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester)

racemic trans-cyclopentanone-3,4-dicarboxylic acid

Downstream raw materials:

3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone

(7,8-trans)-methyl 8-((2-(4-bromophenyl)-2-oxoethyl)carbamoyl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate

(7,8-trans)-methyl 8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate

(S)-methyl 2-((7,8-trans)-8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxaspiro[4.4]nonane-7-carboxamido)-3-methylbutanoate