Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane

Base Information

• Chemical Name: Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane
• CAS No.: 215958-94-4
• Molecular Formula: C₄₅H₇₂O₂SSi
• Molecular Weight: 705.217
• Mol file: 215958-94-4.mol

Synonyms:Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane

Chemical Property of Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane

There total 20 articles about Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-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: 53.0%

(R)-(Z)-{2-[5-(2-chloroethylidene)tetrahydropyran-2-yl]allyloxy}triisopropylsilane (209474-20-4) + (2E,6E,10E)-2,7,11,15-tetramethyl-1-phenylthiohexadeca-2,6,10,14-tetraene (215958-93-3) → Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane (215958-94-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(98)01688-8

Reference yield:

2,7,11,15-Tetramethyl-2(E),6(E),10(E),14-hexadecatetraen-1-ol (158897-33-7) → Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane (215958-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / Bu₃P / pyridine / 1.5 h / 20 °C

2.1: 1,4-diazabicyclo[2.2.2]octane; n-BuLi / tetrahydrofuran; hexane / -78 °C

2.2: 53 percent / tetrahydrofuran; hexane / 5 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; tributylphosphine; In tetrahydrofuran; pyridine; hexane;

DOI:10.1016/S0040-4020(00)01129-7

Reference yield:

triisopropylsilyl chloride (13154-24-0) → Triisopropyl-(2-{(R)-5-[(4E,8E,12E)-4,9,13,17-tetramethyl-3-phenylsulfanyl-octadeca-4,8,12,16-tetraen-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-silane (215958-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C

2.1: 90 percent / DDQ; water / CH₂Cl₂ / 2 h / 20 °C

3.1: 93 percent / NCS; dimethyl sulfide / CH₂Cl₂ / -30 - 0 °C

4.1: 1,4-diazabicyclo[2.2.2]octane; n-BuLi / tetrahydrofuran; hexane / -78 °C

4.2: 53 percent / tetrahydrofuran; hexane / 5 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; N-chloro-succinimide; n-butyllithium; dimethylsulfide; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(00)01129-7

upstream raw materials:

(R)-(Z)-{2-[5-(2-chloroethylidene)tetrahydropyran-2-yl]allyloxy}triisopropylsilane

(2E,6E,10E)-2,7,11,15-tetramethyl-1-phenylthiohexadeca-2,6,10,14-tetraene

triisopropylsilyl chloride

diphenyldisulfane