(1R)-2α-[2-[(1S,2S,3S)-2-(2-Carboxyethyl)-2-methyl-6-methylene-3-(1-methylethenyl)cyclohexyl]ethyl]-1,3-dimethyl-6α-(1-methylethenyl)-3-cyclohexene-1-propionic acid

Base Information

• Chemical Name: (1R)-2α-[2-[(1S,2S,3S)-2-(2-Carboxyethyl)-2-methyl-6-methylene-3-(1-methylethenyl)cyclohexyl]ethyl]-1,3-dimethyl-6α-(1-methylethenyl)-3-cyclohexene-1-propionic acid
• CAS No.: 19954-99-5
• Molecular Formula: C30H46O4
• Molecular Weight: 470.693
• Mol file: 19954-99-5.mol

Synonyms:3-((1S,2S,6S)-2-{2-[(1S,5S,6S)-6-(2-Carboxy-ethyl)-5-isopropenyl-2,6-dimethyl-cyclohex-2-enyl]-ethyl}-6-isopropenyl-1-methyl-3-methylene-cyclohexyl)-propionic acid;lansic acid;

Chemical Property of (1R)-2α-[2-[(1S,2S,3S)-2-(2-Carboxyethyl)-2-methyl-6-methylene-3-(1-methylethenyl)cyclohexyl]ethyl]-1,3-dimethyl-6α-(1-methylethenyl)-3-cyclohexene-1-propionic acid

Chemical Property:

• PSA: 74.60000
• LogP: 7.82580

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R)-2α-[2-[(1S,2S,3S)-2-(2-Carboxyethyl)-2-methyl-6-methylene-3-(1-methylethenyl)cyclohexyl]ethyl]-1,3-dimethyl-6α-(1-methylethenyl)-3-cyclohexene-1-propionic acid

There total 7 articles about (1R)-2α-[2-[(1S,2S,3S)-2-(2-Carboxyethyl)-2-methyl-6-methylene-3-(1-methylethenyl)cyclohexyl]ethyl]-1,3-dimethyl-6α-(1-methylethenyl)-3-cyclohexene-1-propionic 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: 36.0%

3-((1S,2S,6S)-2-{2-[(1S,2S,3S)-2-(2-Cyano-ethyl)-3-isopropenyl-2-methyl-6-methylene-cyclohexyl]-ethyl}-6-isopropenyl-1,3-dimethyl-cyclohex-3-enyl)-propionic acid methyl ester (87453-43-8) → Lansic Acid (19954-99-5)

Guidance literature:

With potassium hydroxide; ethanol; for 3h; Heating;

DOI:10.1021/jo00172a004

Reference yield:

3-[(1S,2S,6S)-2-(2-{(1S,4aR,8aR)-6-[(E)-Hydroxyimino]-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl}-ethyl)-6-isopropenyl-1,3-dimethyl-cyclohex-3-enyl]-propionic acid methyl ester (87453-42-7) → Lansic Acid (19954-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / methanesulfonyl chloride / pyridine / 5 h / 0 °C

2: 36 percent / 20 percent KOH, EtOH / 3 h / Heating

With potassium hydroxide; ethanol; methanesulfonyl chloride; In pyridine;

DOI:10.1021/jo00172a004

Reference yield:

Lansioside C (87453-35-8) → Lansic Acid (19954-99-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 123 mg / methanol, conc. H₂SO₄ / 2 h / Heating

2: 86 percent / Jones reagent / acetone / 0.5 h / 0 °C

3: 93 percent / NH₂OH*HCl / pyridine; ethanol / 2 h / Heating

4: 30 percent / methanesulfonyl chloride / pyridine / 5 h / 0 °C

5: 36 percent / 20 percent KOH, EtOH / 3 h / Heating

With methanol; potassium hydroxide; jones reagent; ethanol; sulfuric acid; hydroxylamine hydrochloride; methanesulfonyl chloride; In pyridine; ethanol; acetone;

DOI:10.1021/jo00172a004

upstream raw materials:

3-((1S,2S,6S)-2-{2-[(1S,2S,3S)-2-(2-Cyano-ethyl)-3-isopropenyl-2-methyl-6-methylene-cyclohexyl]-ethyl}-6-isopropenyl-1,3-dimethyl-cyclohex-3-enyl)-propionic acid methyl ester

3-[(1S,2S,6S)-2-(2-{(1S,4aR,8aR)-6-[(E)-Hydroxyimino]-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl}-ethyl)-6-isopropenyl-1,3-dimethyl-cyclohex-3-enyl]-propionic acid methyl ester

Lansioside C

Lansioside B

Downstream raw materials:

lansic acid dimethyl ester

Refernces