(4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one

Base Information

• Chemical Name: (4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one
• CAS No.: 161197-02-0
• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.392
• Mol file: 161197-02-0.mol

Synonyms:(4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one

Chemical Property of (4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one

There total 3 articles about (4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one 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:

vinyl magnesium bromide (1826-67-1) + (R)-3-methyl-6-(1-methylethylidene)-4-pivaloyloxy-2-cyclohexen-1-one (161197-01-9) → (4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one (161197-02-0) + (4R,5R)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -40 - -30 ℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1248/cpb.42.1393

Reference yield:

2,2-Dimethyl-propionic acid (1R,5R)-5-isopropenyl-2-methyl-cyclohex-2-enyl ester (55378-53-5) → (4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one (161197-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / CrO₃, dimethylpyrazole / CH₂Cl₂ / 15 h / -20 - 0 °C

2: 1.) CuBr*Me₂S, 2.) NaOMe / 1.) THF, -40 deg C, 30 min, 2.) MeOH, 0 deg C, 1.5 h

With 1,3-dimethyl-1H-pyrazole; chromium(VI) oxide; copper(I) bromide dimethylsulfide complex; sodium methylate; In dichloromethane;

DOI:10.1248/cpb.42.1393

Reference yield:

vinyl magnesium bromide (1826-67-1) + (4R,6R)-3-methyl-4-pivaloyloxy-6-(1-methylethenyl)-2-cyclohexen-1-one (161197-00-8) → (4R,5S)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one (161197-02-0) + (4R,5R)-5-methyl-2-(1-methylethylidene)-4-pivaloyloxy-5-vinylcyclohexan-1-one

Guidance literature:

With copper(I) bromide dimethylsulfide complex; sodium methylate; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -40 deg C, 30 min, 2.) MeOH, 0 deg C, 1.5 h;

DOI:10.1248/cpb.42.1393

upstream raw materials:

vinyl magnesium bromide

(R)-3-methyl-6-(1-methylethylidene)-4-pivaloyloxy-2-cyclohexen-1-one

(4R,6R)-3-methyl-4-pivaloyloxy-6-(1-methylethenyl)-2-cyclohexen-1-one

2,2-Dimethyl-propionic acid (1R,5R)-5-isopropenyl-2-methyl-cyclohex-2-enyl ester

Downstream raw materials:

<18R-(8β,9α,10α)>-10-azido-2,6,7,8,9,10-hexahydro-6,6,9-trimethyl-2-(p-toluenesulfonyl)-8-<(2-trimethylsilyl)ethoxy>methoxy-9-vinylnaphth<1,2,3-cd>indole

2,2-Dimethyl-propionic acid (8R,9S)-10-bromo-6,6,9-trimethyl-2-(toluene-4-sulfonyl)-9-vinyl-2,6,7,8,9,10-hexahydro-2-aza-aceanthrylen-8-yl ester

(2S,4R,5S)-5-methyl-2-<1-methyl-1-<1-(p-toluenesulfonyl)-4-indolyl>ethyl>-4-pivaloyloxy-5-vinyl-1-cyclohexanone

<8R-(8β,9α)>-2,6,7,8,9,10-hexahydro-6,6,9-trimethyl-8-pivaloyloxy-2-(p-toluenesulfonyl)-9-vinylnaph<1,2,3-cd>indole