(3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester

Base Information

• Chemical Name: (3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester
• CAS No.: 186265-15-6
• Molecular Formula: C₂₄H₃₂O₁₀
• Molecular Weight: 480.512
• Mol file: 186265-15-6.mol

Synonyms:(3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester

Chemical Property of (3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester

There total 4 articles about (3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl 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:

(3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester (186265-07-6) → (3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester (186265-15-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h; Yield given; Ambient temperature;

DOI:10.1016/S0031-9422(96)00530-4

Reference yield:

3,4,5-trimethoxyphenyl acetic acid (951-82-6) → (3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester (186265-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide, 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

2: H₂ / Pd/C / ethyl acetate / 3 h / Ambient temperature

With dmap; hydrogen; 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1016/S0031-9422(96)00530-4

Reference yield:

syringolide 1 (147716-82-3) → (3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-hydroxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester (186265-15-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / Dowex 50W-X₈*HCl / CH₂Cl₂

2: 87 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide, 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

3: H₂ / Pd/C / ethyl acetate / 3 h / Ambient temperature

With dmap; Dowex 50W-X₈*HCl; hydrogen; 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1016/S0031-9422(96)00530-4

upstream raw materials:

(3,4,5-Trimethoxy-phenyl)-acetic acid (3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl ester

3,4,5-trimethoxyphenyl acetic acid

syringolide 1

(3R,3aS,5R,5aS,8aR)-5-Benzyloxy-3-hydroxy-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-6-one