methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate

Base Information

• Chemical Name: methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate
• CAS No.: 89105-98-6
• Molecular Formula: C₁₇H₂₅BrO₃
• Molecular Weight: 357.288
• Mol file: 89105-98-6.mol

Synonyms:methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate

Chemical Property of methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate

There total 8 articles about methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate 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: 71.0%

(2R)-4-<(1S,6R)-1,6-dimethyl-2-methylene-3-oxocyclohexyl>-2-methyl-butanal (89088-87-9) → methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate (89105-98-6)

Guidance literature:

In 1,2-dimethoxyethane;

DOI:10.1021/jo00181a050

Reference yield:

(+)-(R)-4-methyl-2-cyclohexene-1-one (75337-05-2) → methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate (89105-98-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) copper(I) iodide; 2.) triethylamine / 1.) ether,0 deg C, 45 min; 2.) RT_., 2 h

2: palladium(II) acetate / acetonitrile / 12 h / Ambient temperature

3: 1.) Mg, 2.) copper(I) iodide / 1.) ether, reflux, 1 h, 2.) ether, dimethylsulfide, 0 deg C, then RT_., 1 h, 3.) 0 deg C, 90 min, RT_., 4 h

4: 1.) MeLi / 1.) THF, 0 deg C, 5 min, 2.) TFH, 0 deg C, then RT_., 4 h

5: 51 percent / 1.) ozone, sodium bicarbonate, 2.) dimethyl sulfide / 1.) MeOH, CH₂Cl₂, -78 deg C, RT_., 2.) 12 h

6: 4.51 g / 1.) NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature

With copper(l) iodide; dimethylsulfide; methyllithium; palladium diacetate; sodium hydride; sodium hydrogencarbonate; ozone; magnesium; triethylamine; In 1,2-dimethoxyethane; acetonitrile;

DOI:10.1021/ja00294a046

Reference yield:

(3S,4R)-3,4-dimethyl-3-<(3(R)-methyl-4-pentenyl)-1-cyclohexen-1-yl>carbonate (89088-85-7) → methyl (4R)-2-bromo-6-<(1S,6R)-1,6-dimethyl-3-oxocyclohexyl>-4-methyl-2-hexenoate (89105-98-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) MeLi / 1.) THF, 0 deg C, 5 min, 2.) TFH, 0 deg C, then RT_., 4 h

2: 51 percent / 1.) ozone, sodium bicarbonate, 2.) dimethyl sulfide / 1.) MeOH, CH₂Cl₂, -78 deg C, RT_., 2.) 12 h

3: 4.51 g / 1.) NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature

With dimethylsulfide; methyllithium; sodium hydride; sodium hydrogencarbonate; ozone; In 1,2-dimethoxyethane;

DOI:10.1021/ja00294a046

upstream raw materials:

(2R)-4-<(1S,6R)-1,6-dimethyl-2-methylene-3-oxocyclohexyl>-2-methyl-butanal

(+)-(R)-4-methyl-2-cyclohexene-1-one

(3S,4R)-2-<(dimethylamino)methyl>-3,4-dimethyl-3-<(3(R)-methyl-4-pentenyl)>-1-cyclohexanone

(3S,4R)-3,4-dimethyl-3-<(3(R)-methyl-4-pentenyl)-1-cyclohexen-1-yl>carbonate

Downstream raw materials:

(2R)-4-<(1S,6R)-1,6-dimethyl-2-methylene-3-oxocyclohexyl>-2-methyl-butanal