Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl ester

Base Information

• Chemical Name: Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl ester
• CAS No.: 225928-44-9
• Molecular Formula: C₄₀H₅₀O₉
• Molecular Weight: 674.832
• Mol file: 225928-44-9.mol

Synonyms:Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl ester

Chemical Property of Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl ester

There total 12 articles about Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl 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:

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (190712-24-4) → Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl ester (225928-44-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / imidazole / dimethylformamide

2: 99 percent / H₂ / 5 percent Pd/C / ethyl acetate

3: I₂, imidazole, Ph₃P / benzene

4: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

5: K₂CO₃ / methanol

6: 1.) Cp₂Zr(H)Cl; 2.) (Ph₃P)2PdCl₂, DIBAL / 1.) THF; 2.) THF

7: TBAF / tetrahydrofuran

8: (COCl)2, Et₃N, DMSO / CH₂Cl₂

9: (cyclohexyl)2BCl, Me₂NEt / diethyl ether

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(99)00411-6

Reference yield:

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane (225928-52-9) → Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl ester (225928-44-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / H₂ / 5 percent Pd/C / ethyl acetate

2: I₂, imidazole, Ph₃P / benzene

3: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

4: K₂CO₃ / methanol

5: 1.) Cp₂Zr(H)Cl; 2.) (Ph₃P)2PdCl₂, DIBAL / 1.) THF; 2.) THF

6: TBAF / tetrahydrofuran

7: (COCl)2, Et₃N, DMSO / CH₂Cl₂

8: (cyclohexyl)2BCl, Me₂NEt / diethyl ether

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(99)00411-6

Reference yield:

para-iodoanisole (696-62-8) → Benzoic acid (1R,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-4-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-methyl-2-oxo-butyl ester (225928-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Cp₂Zr(H)Cl; 2.) (Ph₃P)2PdCl₂, DIBAL / 1.) THF; 2.) THF

2: TBAF / tetrahydrofuran

3: (COCl)2, Et₃N, DMSO / CH₂Cl₂

4: (cyclohexyl)2BCl, Me₂NEt / diethyl ether

With bis-triphenylphosphine-palladium(II) chloride; Schwartz's reagent; oxalyl dichloride; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(99)00411-6

upstream raw materials:

Benzoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-2-oxo-propyl ester

(4R,5S)-5-[(E)-(S)-7-(4-Methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

para-iodoanisole

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

Downstream raw materials:

((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

2,2-Dimethyl-propionic acid (2S,3S)-3-azido-2-(4-methoxy-benzyloxy)-3-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl ester

2,2-Dimethyl-propionic acid (2R,3R)-3-hydroxy-2-(4-methoxy-benzyloxy)-3-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl ester

(1R,2R)-2-(4-Methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propane-1,3-diol