[(Z)-(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-9,9-bis-ethylsulfanyl-non-3-enyloxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [(Z)-(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-9,9-bis-ethylsulfanyl-non-3-enyloxy]-tert-butyl-diphenyl-silane
• CAS No.: 479231-63-5
• Molecular Formula: C₃₄H₄₉BrOS₂Si
• Molecular Weight: 645.884
• Mol file: 479231-63-5.mol

Synonyms:

Chemical Property of [(Z)-(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-9,9-bis-ethylsulfanyl-non-3-enyloxy]-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(Z)-(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-9,9-bis-ethylsulfanyl-non-3-enyloxy]-tert-butyl-diphenyl-silane

There total 10 articles about [(Z)-(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-9,9-bis-ethylsulfanyl-non-3-enyloxy]-tert-butyl-diphenyl-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:

(2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trien-1-ol (479231-62-4) → [(Z)-(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-9,9-bis-ethylsulfanyl-non-3-enyloxy]-tert-butyl-diphenyl-silane (479231-63-5)

Guidance literature:

With carbon tetrabromide; temephos; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1016/S0040-4039(02)01206-6

Reference yield:

1-bromo-6-hexanol (4286-55-9) → [(Z)-(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-9,9-bis-ethylsulfanyl-non-3-enyloxy]-tert-butyl-diphenyl-silane (479231-63-5)

Guidance literature:

Multi-step reaction with 6 steps

1: PCC; Al₂O₃ / CH₂Cl₂ / 0.5 h / 20 °C

2: BF₃*Et₂O / 20 °C

3: acetonitrile / 48 h / Heating

4: 70 percent / n-Buli / tetrahydrofuran / 2 h / -78 - 20 °C

5: DIBAL-H / CH₂Cl₂ / 1 h / -60 - -20 °C

6: DIPHOS; CBr₄ / CH₂Cl₂ / 0.33 h / 0 °C

With aluminum oxide; n-butyllithium; carbon tetrabromide; temephos; boron trifluoride diethyl etherate; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(02)01206-6

Reference yield:

tert-Butyl-[(R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propoxy]-diphenyl-silane (85593-59-5) → [(Z)-(R)-1-((1E,3E)-5-Bromo-penta-1,3-dienyl)-9,9-bis-ethylsulfanyl-non-3-enyloxy]-tert-butyl-diphenyl-silane (479231-63-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 4 h / 50 °C

2: 88 percent / Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.33 h / -40 - -30 °C

3: 83 percent / LiN(SiMe₃)2 / -78 - 20 °C

4: 87 percent / periodic acid / diethyl ether; tetrahydrofuran / 0.05 h / 0 - 20 °C

5: 70 percent / n-Buli / tetrahydrofuran / 2 h / -78 - 20 °C

6: DIBAL-H / CH₂Cl₂ / 1 h / -60 - -20 °C

7: DIPHOS; CBr₄ / CH₂Cl₂ / 0.33 h / 0 °C

With lead(IV) acetate; n-butyllithium; carbon tetrabromide; temephos; diisobutylaluminium hydride; sodium carbonate; periodic acid; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; 3: Wittig-Horner reaction;

DOI:10.1016/S0040-4039(02)01206-6

upstream raw materials:

(2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trien-1-ol

1-bromo-6-hexanol

tert-Butyl-[(R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propoxy]-diphenyl-silane

6-bromo-1,1-bis-ethylsulfanyl-hexane

Downstream raw materials:

Benzoic acid (2Z,4E,6E,10Z)-(1S,8R)-16,16-bis-ethylsulfanyl-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester

Benzoic acid (2Z,4E,6E,10Z)-(1S,8R)-8-(tert-butyl-diphenyl-silanyloxy)-16,16-bis-ethylsulfanyl-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester