4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid

Base Information

• Chemical Name: 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid
• CAS No.: 204326-53-4
• Molecular Formula: C₁₄H₂₄O₄
• Molecular Weight: 256.342
• Mol file: 204326-53-4.mol

Synonyms:4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid

Chemical Property of 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid

There total 4 articles about 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic 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: 88.0%

succinic acid anhydride (108-30-5) + (1S,2R,5S)-(+)-menthol (15356-60-2) → 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid (204326-53-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo980011z

Reference yield:

succinic acid anhydride (108-30-5) + menthol (15356-70-4) → (1S,2R,5S)-(+)-menthol (15356-60-2) + (-)-menthol (2216-51-5) + L-menthylsuccinic acid (77341-67-4) + 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid (204326-53-4)

Guidance literature:

With Candida cylindracea lipase; In diethyl ether; at 20 ℃; for 24h; Schlenk technique; Resolution of racemate; Enzymatic reaction;

DOI:10.1007/s11164-018-3525-7

Reference yield:

dl-menthyl succinate (6070-20-8,75363-56-3,77341-67-4) → (-)-menthol (2216-51-5) + 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid (204326-53-4)

Guidance literature:

With Bacillus subtilis esterase; In ethanol; at 30 ℃; for 24h; pH=7.2; optical yield given as %ee; enantioselective reaction; aq. phosphate buffer;

DOI:10.1002/adsc.200800412

upstream raw materials:

succinic acid anhydride

(1S,2R,5S)-(+)-menthol

dl-menthyl succinate

menthol

Refernces

• 1、 E Sana, Auj,Khan, Sher W.,Ambreen, Nida,Arfan, Muhammad,Zaidi, Javid H.,Khan, Khalid M.,Perveen, Shahnaz,Miana, Ghulam A.. "Asymmetric induction via metalation of succinic esters and amide using S(+) menthol and R(+) 1-Phenylethylamine as chiral auxiliaries". . p. 632 - 638. Retrieved 2013/02/25.
• 2、 Procopiou, Panayiotis A.,Baugh, Simon P.D.,Flack, Stephen S.,Inglis, Graham G.A.. "An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate". . p. 2342 - 2347. Retrieved 2007/10/03.