Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 145369-07-9
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.461
• Mol file: 145369-07-9.mol

Synonyms:Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester

There total 4 articles about Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester 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: 58.0%

(2R,5R)-5-isopropenyl-2-methylcyclohexanone (5524-05-0) + 3-deoxy-2,5-di-O-benzoylthreo-γ-lactone (145369-04-6) → Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester (145369-07-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; In tetrahydrofuran; at -78 - 23 ℃;

DOI:10.1021/jo00067a045

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester (145369-07-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / pyridine / CHCl₃ / 1 h

2: 68 percent / Et₃N, H₂ / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

3: 58 percent / SmI₂, HMPA / tetrahydrofuran / -78 - 23 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; chloroform; ethyl acetate;

DOI:10.1021/jo00067a045

Reference yield:

C26H20O8 (15397-14-5) → Benzoic acid (2S,4S)-4-((1S,2R,5R)-1-hydroxy-5-isopropenyl-2-methyl-cyclohexyl)-5-oxo-tetrahydro-furan-2-ylmethyl ester (145369-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / Et₃N, H₂ / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

2: 58 percent / SmI₂, HMPA / tetrahydrofuran / -78 - 23 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo00067a045

upstream raw materials:

(2R,5R)-5-isopropenyl-2-methylcyclohexanone

3-deoxy-2,5-di-O-benzoylthreo-γ-lactone

benzoyl chloride

C₂₆H₂₀O₈