(1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol

Base Information

• Chemical Name: (1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol
• CAS No.: 472986-74-6
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.354
• Mol file: 472986-74-6.mol

Synonyms:(1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol

Chemical Property of (1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol

There total 6 articles about (1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol 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:

Triethyl-{(1R,6R)-6-[1-((2R,3R)-3-isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enyloxy}-silane (472986-73-5) → (1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol (472986-74-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/jo0203140

Reference yield:

Benzoic acid (E)-(S)-5-methyl-1-((S)-4-methyl-2-oxo-cyclohex-3-enyl)-hex-2-enyl ester → (1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol (472986-74-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / -78 - -18 °C

1.2: imidazole / dimethylformamide / 2 h / 0 °C

1.3: diisobutylaluminium hydride / CH₂Cl₂; toluene / 1.5 h / -78 °C

2.1: VO(acac)2; t-BuOOH / CH₂Cl₂; toluene / 2.5 h / 0 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

4.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C

5.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 1.5 h / 0 °C

6.1: n-Bu₄NF / tetrahydrofuran / 3 h / 0 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 3.1: Dess-Martin oxidation;

DOI:10.1021/jo0203140

Reference yield:

((2S,3R)-3-Isobutyl-oxiranyl)-((1S,2R)-4-methyl-2-triethylsilanyloxy-cyclohex-3-enyl)-methanone (472986-71-3) → (1R,6R)-6-[1-((2R,3R)-3-Isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enol (472986-74-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; diethyl ether / 1 h / 0 °C

2: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 1.5 h / 0 °C

3: n-Bu₄NF / tetrahydrofuran / 3 h / 0 °C

With tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1021/jo0203140

upstream raw materials:

Triethyl-{(1R,6R)-6-[1-((2R,3R)-3-isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enyloxy}-silane

(E)-(S)-5-Methyl-1-((1R,2R)-4-methyl-2-triethylsilanyloxy-cyclohex-3-enyl)-hex-2-en-1-ol

((2S,3R)-3-Isobutyl-oxiranyl)-((1S,2R)-4-methyl-2-triethylsilanyloxy-cyclohex-3-enyl)-methanone

(R)-((2R,3R)-3-Isobutyl-oxiranyl)-((1R,2R)-4-methyl-2-triethylsilanyloxy-cyclohex-3-enyl)-methanol

Downstream raw materials:

(+)-cheimonophyllon E