(4R*,5S*)-3,3-bis(methoxycarbonyl)-2,5-dimethyl-4-phenylcyclopentanone

Base Information

• Chemical Name: (4R*,5S*)-3,3-bis(methoxycarbonyl)-2,5-dimethyl-4-phenylcyclopentanone
• CAS No.: 141023-19-0
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343
• Mol file: 141023-19-0.mol

Synonyms:

Chemical Property of (4R*,5S*)-3,3-bis(methoxycarbonyl)-2,5-dimethyl-4-phenylcyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R*,5S*)-3,3-bis(methoxycarbonyl)-2,5-dimethyl-4-phenylcyclopentanone

There total 7 articles about (4R*,5S*)-3,3-bis(methoxycarbonyl)-2,5-dimethyl-4-phenylcyclopentanone 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: 98.0%

2,4-Dimethyl-3-oxo-5-phenyl-cyclopentane-1,1-dicarboxylic acid dimethyl ester (141023-19-0,141115-84-6,141115-85-7,141115-86-8) → (4R*,5S*)-3,3-bis(methoxycarbonyl)-2,5-dimethyl-4-phenylcyclopentanone (141023-19-0,141115-84-6,141115-85-7,141115-86-8)

Guidance literature:

With sodium methylate; In methanol; for 48h; Ambient temperature;

DOI:10.1055/s-1992-34152

Reference yield:

(Z)-3-((trimethylsilyl)methyl)pent-3-en-2-ol (141023-16-7) → 2,4-Dimethyl-3-oxo-5-phenyl-cyclopentane-1,1-dicarboxylic acid dimethyl ester (141023-19-0,141115-84-6,141115-85-7,141115-86-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / DMAP, pyridine / CH₂Cl₂ / 6 h / 0 deg C to RT

2: 69 percent / Pd(OAc)2, (i-PrO)3P / toluene / 6 h / 100 °C

3: 1) O₃, 2) Me₂S / 1) CH₂Cl₂, MeOH, -78 deg C, 2) RT, 12h

With pyridine; dmap; dimethylsulfide; ozone; palladium diacetate; triisopropyl phosphite; In dichloromethane; toluene;

DOI:10.1055/s-1992-34152

Reference yield:

(Z)-3-((trimethylsilyl)methyl)pent-3-en-2-ol (141023-16-7) → (4R*,5S*)-3,3-bis(methoxycarbonyl)-2,5-dimethyl-4-phenylcyclopentanone (141023-19-0,141115-84-6,141115-85-7,141115-86-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / DMAP, pyridine / CH₂Cl₂ / 6 h / 0 deg C to RT

2: 69 percent / Pd(OAc)2, (i-PrO)3P / toluene / 6 h / 100 °C

3: 1) O₃, 2) Me₂S / 1) CH₂Cl₂, MeOH, -78 deg C, 2) RT, 12h

4: 98 percent / NaOMe / methanol / 48 h / Ambient temperature

With pyridine; dmap; dimethylsulfide; sodium methylate; ozone; palladium diacetate; triisopropyl phosphite; In methanol; dichloromethane; toluene;

DOI:10.1055/s-1992-34152

upstream raw materials:

2,4-Dimethyl-3-methylene-5-phenyl-cyclopentane-1,1-dicarboxylic acid dimethyl ester

(Z)-3-((trimethylsilyl)methyl)pent-3-en-2-ol

methyl (Z)-1-methyl-2-trimethylsilylmethyl-2-butenyl carbonate

2,4-Dimethyl-3-oxo-5-phenyl-cyclopentane-1,1-dicarboxylic acid dimethyl ester

Downstream raw materials:

(4R*,5S*)-3,3-bis(methoxycarbonyl)-2,5-dimethyl-4-phenylcyclopentanone