tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane

Base Information

• Chemical Name: tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane
• CAS No.: 82679-76-3
• Molecular Formula: C₃₆H₄₀OSi
• Molecular Weight: 516.798
• Mol file: 82679-76-3.mol

Synonyms:tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane

Chemical Property of tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane

There total 18 articles about tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-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: 75.0%

diethyl (E)-cinnamylphosphonate (52378-69-5) + [(1R,6R,7S,8R)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetaldehyde (82679-75-2) → tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane (82679-76-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; for 24h; -78 deg C -> 25 deg C;

DOI:10.1021/ja00384a077

Reference yield:

(2E,8E)-deca-2,8-diene-4,6-diyne-1,10-diol (7199-98-6) → tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane (82679-76-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 55 percent / hydrogen, qunoline / Lindlar catalyst / CH₂Cl₂; methanol / 25 °C

2: I₂, K₂CO₃ / CH₂Cl₂ / 2 h / -20 deg C -> 0 deg C

3: imidazole / dimethylformamide / 2 h / 25 °C

4: Zn dust, AcOH / 25 °C

5: CBr₄, Ph₃P / CH₂Cl₂ / 0 °C

6: hexamethylphosphoric acid triamide / 25 °C

7: 1.) Dibal / 1.) CH₂Cl₂, -78 deg C, 2.) mild acid hydrolysis

8: 75 percent / LDA / tetrahydrofuran / 24 h / -78 deg C -> 25 deg C

With 1H-imidazole; quinoline; carbon tetrabromide; hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; acetic acid; triphenylphosphine; zinc; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00384a077

Reference yield:

(2E,8E)-deca-2,8-diene-4,6-diyne-1,10-diol (7199-98-6) → tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2Z,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane (82679-76-3,82863-38-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 55 percent / hydrogen, qunoline / Lindlar catalyst / CH₂Cl₂; methanol / 25 °C

2: I₂, K₂CO₃ / CH₂Cl₂ / 2 h / -20 deg C -> 0 deg C

3: imidazole / dimethylformamide / 2 h / 25 °C

4: Zn dust, AcOH / 25 °C

5: CBr₄, Ph₃P / CH₂Cl₂ / 0 °C

6: hexamethylphosphoric acid triamide / 25 °C

7: 1.) Dibal / 1.) CH₂Cl₂, -78 deg C, 2.) mild acid hydrolysis

With 1H-imidazole; quinoline; carbon tetrabromide; hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; acetic acid; triphenylphosphine; zinc; Lindlar's catalyst; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00384a077

upstream raw materials:

[(1R,6R,7S,8R)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetaldehyde

cinnamylidenetriphenylphosphorane

(2E,8E)-deca-2,8-diene-4,6-diyne-1,10-diol

((1R,6S,7S,8S)-8-Hydroxymethyl-bicyclo[4.2.0]octa-2,4-dien-7-yl)-methanol

Downstream raw materials:

[(1S,6S,7S,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-methanol

tert-Butyl-diphenyl-((1S,1aR,2aS,5R,5aR,7aS,7bS,7cS)-5-phenyl-1a,2,2a,5,5a,7a,7b,7c-octahydro-1H-cyclobuta[bc]acenaphthylen-1-ylmethoxy)-silane

(1S,6S,7S,8R)-7-Bromomethyl-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-diene

[(1R,6S,7R,8R)-8-((2E,4E)-5-Phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-yl]-acetonitrile