(3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid

Base Information

• Chemical Name: (3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid
• CAS No.: 380599-35-9
• Molecular Formula: C₂₅H₃₂O₆
• Molecular Weight: 428.525
• Mol file: 380599-35-9.mol

Synonyms:(3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid

Chemical Property of (3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid

There total 7 articles about (3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic 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: 85.0%

Acetic acid 3-acetoxy-2-((1R,6R)-3-formyl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-phenyl ester (380495-74-9) → (3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid (380599-35-9)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; at 20 ℃; for 5h;

DOI:10.1039/b416943c

Reference yield:

(3R,4R)-3-[2,6-dihydroxy-4-pentylphenyl]-2-hydroxy-4-isopropenyl-1-methylenecyclohexane (380495-68-1) → (3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid (380599-35-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / pyridine / 18 h / 20 °C

2: 90 percent / TMSBr; ZnI₂ / CH₂Cl₂ / 4 h / 20 °C

3: 35 percent / 18-crown-6; K₂CrO₄; 4 Angstroem molecular sieves / hexamethylphosphoric acid triamide / 2 h / 110 °C

4: 85 percent / NaClO₂; 2-methyl-2-butene; aq. KH₂PO₄ / 5 h / 20 °C

With pyridine; sodium chlorite; potassium chromate; potassium dihydrogenphosphate; 2-methyl-but-2-ene; 18-crown-6 ether; trimethylsilyl bromide; 4 A molecular sieve; zinc(II) iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1039/b416943c

Reference yield:

Acetic acid 3-acetoxy-2-((1R,6R)-3-bromomethyl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-phenyl ester (380495-72-7) → (3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid (380599-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / 18-crown-6; K₂CrO₄; 4 Angstroem molecular sieves / hexamethylphosphoric acid triamide / 2 h / 110 °C

2: 85 percent / NaClO₂; 2-methyl-2-butene; aq. KH₂PO₄ / 5 h / 20 °C

With sodium chlorite; potassium chromate; potassium dihydrogenphosphate; 2-methyl-but-2-ene; 18-crown-6 ether; 4 A molecular sieve; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1039/b416943c

upstream raw materials:

Acetic acid 3-acetoxy-2-((1R,6R)-3-formyl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-phenyl ester

(3R,4R)-3-[2,6-dihydroxy-4-pentylphenyl]-2-hydroxy-4-isopropenyl-1-methylenecyclohexane

Acetic acid 3-acetoxy-2-((1R,6R)-3-bromomethyl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-phenyl ester

(3R,4R)-3-[2,6-diacetoxy-4-pentylphenyl]-2-acetoxy-4-isopropenyl-1-methylenecyclohexane

Refernces