(R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 237736-50-4
• Molecular Formula: C₁₈H₃₀O₄
• Molecular Weight: 310.434
• Mol file: 237736-50-4.mol

Synonyms:(R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property of (R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester

There total 8 articles about (R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl 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: 46.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + Trifluoro-methanesulfonic acid (R)-4-[(S)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enyl ester (237736-51-5) → (R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester (237736-50-4)

Guidance literature:

With triethylamine; triphenylphosphine; palladium diacetate; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00713-3

Reference yield:

3-(3-hydroxy-cyclopentyl)-N-methoxy-N-methyl-butyramide → (R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester (237736-50-4)

Guidance literature:

Multi-step reaction with 9 steps

1: tetrahydrofuran

2: pTsOH / benzene / Heating

3: pyridinium chlorochromate (PCC), NaOAc / CH₂Cl₂

5: H₂ / 10 percent Pd/C / ethyl acetate

6: NaH / tetrahydrofuran

7: 68 percent / NaBH₄ / methanol

8: Et₃N / CH₂Cl₂

9: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂

With sodium tetrahydroborate; hydrogen; sodium acetate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(99)00713-3

Reference yield:

(R)-5-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-2-enone (237736-46-8) → (R)-4-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enecarboxylic acid methyl ester (237736-50-4)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / 10 percent Pd/C / ethyl acetate

2: NaH / tetrahydrofuran

3: 68 percent / NaBH₄ / methanol

4: Et₃N / CH₂Cl₂

5: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂

With sodium tetrahydroborate; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(99)00713-3

upstream raw materials:

methanol

carbon monoxide

Trifluoro-methanesulfonic acid (R)-4-[(S)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-1-enyl ester

(R)-5-[(S)-2-(2-Isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-cyclohex-2-enone

Downstream raw materials:

(+)-epijuvabione