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

Base Information

• Chemical Name: menthyl (1S,2S,3S)-2-carboxy-3-methylcyclopropane-1-carboxylate
• CAS No.: 153618-34-9
• Molecular Formula: C₁₆H₂₆O₄
• Molecular Weight: 282.38
• Mol file: 153618-34-9.mol

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

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

There total 1 articles about menthyl (1S,2S,3S)-2-carboxy-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: 83.0%

dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate (130799-04-1) → menthyl (1S,2S,3S)-2-carboxy-3-methylcyclopropane-1-carboxylate (153618-34-9)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; ethanol; water; for 84h; Ambient temperature;

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

Reference yield: 100.0%

menthyl (1S,2S,3S)-2-carboxy-3-methylcyclopropane-1-carboxylate (153618-34-9) → menthyl (1S,2S,3S)-2-hydroxymethyl-3-methylcyclopropane-1-carboxylate (153618-35-0)

Guidance literature:

With B₂H₆-THF; Ambient temperature;

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

Reference yield:

menthyl (1S,2S,3S)-2-carboxy-3-methylcyclopropane-1-carboxylate (153618-34-9) → (+)-ambruticin S (58857-02-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 100 percent / B₂H₆*THF / Ambient temperature

2: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

3: 98 percent / Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

4: 90 percent / DIBALH / toluene; hexane / 1.) -78 deg C, 10 min; 2.) 0 deg C, 30 min

5: 90 percent / Et₃N, DMAP / dimethylformamide / 72 h / Ambient temperature

6: 92 percent / nBuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

7: 49 percent / 1.) DIBALH / hexane; tetrahydrofuran / 1.) 50 deg C, 2 h; 2.) -20 deg C, 10 min; RT, 30 min

8: 92 percent / p-toluenesulfonic acid / CH₂Cl₂; methanol / 2 h / Ambient temperature

9: 90 percent / Dess-Martin's periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 51 percent / nBuLi / diethyl ether; hexane / 1.) 0 deg C, 10 min; 2.) -42 deg C, 135 min

11: 6percent Na(Hg) / methanol; tetrahydrofuran / 3.5 h / -35 °C

12: LiOH / tetrahydrofuran; H₂O / 18 h / Ambient temperature

13: Li/NH₃(l) / ethanol / 0.5 h / -78 °C

With dmap; lithium hydroxide; n-butyllithium; sodium amalgam; B₂H₆-THF; ammonia; lithium; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

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

Downstream raw materials:

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

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

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

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