menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate

Base Information

• Chemical Name: menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate
• CAS No.: 130799-05-2
• Molecular Formula: C₁₆H₂₆O₃
• Molecular Weight: 266.381
• Mol file: 130799-05-2.mol

Synonyms:menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate

Chemical Property of menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate

There total 4 articles about menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate 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: 96.0%

menthyl (1S,2S,3S)-2-hydroxymethyl-3-methylcyclopropane-1-carboxylate (153618-35-0) → menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate (130799-05-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4020(01)88025-X

Reference yield:

bis(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl butanedioate (34212-59-4,96149-05-2) → menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate (130799-05-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / 2,2,6,6-tetramethylpiperidine, n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 65 min; 2.) -78 deg C, 9.5 h

2: 83 percent / 10percent KOH / tetrahydrofuran; ethanol; H₂O / 84 h / Ambient temperature

3: 100 percent / B₂H₆*THF / Ambient temperature

4: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

With 2,2,6,6-tetramethyl-piperidine; potassium hydroxide; n-butyllithium; B₂H₆-THF; Dess-Martin periodane; In tetrahydrofuran; ethanol; hexane; dichloromethane; water;

DOI:10.1016/S0040-4020(01)88025-X

Reference yield:

dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate (130799-04-1) → menthyl (1S,2S,3S)-2-formyl-3-methylcyclopropane-1-carboxylate (130799-05-2)

Guidance literature:

Yield given. Multistep reaction;

upstream raw materials:

dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate

menthyl (1S,2S,3S)-2-hydroxymethyl-3-methylcyclopropane-1-carboxylate

bis(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl butanedioate

menthyl (1S,2S,3S)-2-carboxy-3-methylcyclopropane-1-carboxylate

Downstream raw materials:

(1S,2S,3S)-3-ethynyl-2-methylcyclopropylmethyl triphenylmethyl ether

(+)-ambruticin S

5β,6α-dibenzyloxypolyangioic acid

methyl 5β,6α-dibenzyloxypolyangioate