(2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester

Base Information

• Chemical Name: (2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester
• CAS No.: 479231-61-3
• Molecular Formula: C₃₅H₅₀O₃S₂Si
• Molecular Weight: 610.998
• Mol file: 479231-61-3.mol

Synonyms:(2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester

Chemical Property of (2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester

There total 7 articles about (2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester 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: 70.0%

(2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-8-oxo-octa-2,4-dienoic acid methyl ester (479231-59-9) + (6,6-bis-ethylsulfanyl-hexyl)-triphenyl-phosphonium; bromide → (2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester (479231-61-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 2h;

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

Reference yield:

1-bromo-6-hexanol (4286-55-9) → (2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester (479231-61-3)

Guidance literature:

Multi-step reaction with 4 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

With aluminum oxide; n-butyllithium; boron trifluoride diethyl etherate; 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) → (2E,4E,8Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-14,14-bis-ethylsulfanyl-tetradeca-2,4,8-trienoic acid methyl ester (479231-61-3)

Guidance literature:

Multi-step reaction with 5 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

With lead(IV) acetate; n-butyllithium; 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)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-8-oxo-octa-2,4-dienoic acid methyl ester

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)-8-(tert-butyl-diphenyl-silanyloxy)-16,16-bis-ethylsulfanyl-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester

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

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

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