(2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-silane

Base Information

• Chemical Name: (2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-silane
• CAS No.: 337971-37-6
• Molecular Formula: C₃₅H₅₆O₂SSi
• Molecular Weight: 568.98
• Mol file: 337971-37-6.mol

Synonyms:

Chemical Property of (2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-silane

There total 16 articles about (2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-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:

triisopropylsilyl chloride (13154-24-0) → (2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-silane (337971-37-6)

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: 89 percent / tetrahydrofuran; hexane / 1.5 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

Reference yield:

(R)-(Z)-2-[5-(2-hydroxyethylidene)tetrahydropyran-2-yl]propan-2-ol (209474-16-8) → (2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-silane (337971-37-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / triethylamine / CH₂Cl₂ / 12 h / 20 °C

2.1: 41 percent / 4-dimethylaminopyridine; triethylamine; MsCl / CH₂Cl₂ / 2 h / 20 °C

3.1: 91 percent / mCPBA / CH₂Cl₂ / 72 h / -10 °C

4.1: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C

5.1: 99 percent / NaH / dimethylformamide / 7 h / 20 °C

6.1: 78 percent / aluminum triisopropoxide / toluene / 36 h / Heating

7.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C

8.1: 90 percent / DDQ; water / CH₂Cl₂ / 2 h / 20 °C

9.1: 93 percent / NCS; dimethyl sulfide / CH₂Cl₂ / -30 - 0 °C

10.1: 1,4-diazabicyclo[2.2.2]octane; n-BuLi / tetrahydrofuran; hexane / -78 °C

10.2: 89 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; dmap; sodium hydroxide; N-chloro-succinimide; n-butyllithium; dimethylsulfide; water; aluminum isopropoxide; sodium hydride; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

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

Reference yield:

(R)-(Z)-2-(6-isopropenyltetrahydropyran-3-ylidene)ethyl benzoate (337971-07-0) → (2-{(R)-5-[(E)-5,9-Dimethyl-3-phenylsulfanyl-deca-4,8-dien-(Z)-ylidene]-tetrahydro-pyran-2-yl}-allyloxy)-triisopropyl-silane (337971-37-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 91 percent / mCPBA / CH₂Cl₂ / 72 h / -10 °C

2.1: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 1 h / 20 °C

3.1: 99 percent / NaH / dimethylformamide / 7 h / 20 °C

4.1: 78 percent / aluminum triisopropoxide / toluene / 36 h / Heating

5.1: 100 percent / imidazole / dimethylformamide / 7 h / 20 °C

6.1: 90 percent / DDQ; water / CH₂Cl₂ / 2 h / 20 °C

7.1: 93 percent / NCS; dimethyl sulfide / CH₂Cl₂ / -30 - 0 °C

8.1: 1,4-diazabicyclo[2.2.2]octane; n-BuLi / tetrahydrofuran; hexane / -78 °C

8.2: 89 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; sodium hydroxide; N-chloro-succinimide; n-butyllithium; dimethylsulfide; water; aluminum isopropoxide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

triisopropylsilyl chloride

(R)-(Z)-2-[5-(2-hydroxyethylidene)tetrahydropyran-2-yl]propan-2-ol

(6'R,1''RS)-(2Z)-2-[6'-(1''-methyloxiranyl)tetrahydropyran-3'-ylidene]ethanol

(R)-(Z)-2-[2-(2,2,5,5-tetramethyl[1,3]dioxolan-4-yl)ethyl]but-2-ene-1,4-diol