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

Base Information

• Chemical Name: Triethyl-{(1R,6R)-6-[1-((2R,3R)-3-isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enyloxy}-silane
• CAS No.: 472986-73-5
• Molecular Formula: C₂₁H₃₈O₂Si
• Molecular Weight: 350.617
• Mol file: 472986-73-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

1-((2S,3R)-3-Isobutyl-oxiranyl)-1-((1S,2R)-4-methyl-2-triethylsilanyloxy-cyclohex-3-enyl)-2-trimethylsilanyl-ethanol (472986-72-4) → Triethyl-{(1R,6R)-6-[1-((2R,3R)-3-isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enyloxy}-silane (472986-73-5)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 0 ℃; for 1.5h;

DOI:10.1021/jo0203140

Reference yield:

triethylsilyl chloride (994-30-9) → Triethyl-{(1R,6R)-6-[1-((2R,3R)-3-isobutyl-oxiranyl)-vinyl]-3-methyl-cyclohex-2-enyloxy}-silane (472986-73-5)

Guidance literature:

Multi-step reaction with 5 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

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

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

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jo0203140

upstream raw materials:

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

triethylsilyl chloride

(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

Downstream raw materials:

(+)-cheimonophyllon E

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