((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide

Base Information

• Chemical Name: ((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide
• CAS No.: 1297531-38-4
• Molecular Formula: C₆₆H₁₁₀O₄PSi₄*I
• Molecular Weight: 1237.82
• Mol file: 1297531-38-4.mol

Synonyms:((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide

Chemical Property of ((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide

There total 15 articles about ((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide 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:

tert-butyl(((2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentyl)oxy)diphenylsilane (1297531-62-4) → ((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide (1297531-38-4)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

2: C₅H₅N*HO₃S; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

3: chromium dichloride; nickel dichloride / tetrahydrofuran; dimethyl sulfoxide / 17 h / 20 °C / Inert atmosphere; Large scale reaction

4: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

5: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C

6: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; acetonitrile / 20 °C / Darkness

7: lithium carbonate / acetonitrile; benzene / 60 h / Reflux

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; C₅H₅N*HO₃S; tetrabutyl ammonium fluoride; water; iodine; lithium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene; 3: Nozaki-Hiyama-Kishi reaction;

DOI:10.1021/ol200834p

Reference yield:

(2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol (765915-18-2) → ((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide (1297531-38-4)

Guidance literature:

Multi-step reaction with 6 steps

1: C₅H₅N*HO₃S; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

2: chromium dichloride; nickel dichloride / tetrahydrofuran; dimethyl sulfoxide / 17 h / 20 °C / Inert atmosphere; Large scale reaction

3: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

4: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C

5: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; acetonitrile / 20 °C / Darkness

6: lithium carbonate / acetonitrile; benzene / 60 h / Reflux

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; C₅H₅N*HO₃S; water; iodine; lithium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene; 2: Nozaki-Hiyama-Kishi reaction;

DOI:10.1021/ol200834p

Reference yield:

(S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one (1297531-60-2) → ((2S,4S,8S,9S,E)-9-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2,4,8-trimethyl-5,9-bis((triethylsilyl)oxy)non-6-en-1-yl)triphenylphosphonium iodide (1297531-38-4)

Guidance literature:

Multi-step reaction with 11 steps

1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h

2: lithium hexamethyldisilazane / tetrahydrofuran / 6.17 h / -78 - 0 °C / Inert atmosphere

3: lithium borohydride / tetrahydrofuran; water / 6 h / 0 °C

4: CSA / dichloromethane / 24 h / 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

6: C₅H₅N*HO₃S; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

7: chromium dichloride; nickel dichloride / tetrahydrofuran; dimethyl sulfoxide / 17 h / 20 °C / Inert atmosphere; Large scale reaction

8: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

9: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C

10: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; acetonitrile / 20 °C / Darkness

11: lithium carbonate / acetonitrile; benzene / 60 h / Reflux

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; lithium borohydride; palladium 10% on activated carbon; C₅H₅N*HO₃S; tetrabutyl ammonium fluoride; water; hydrogen; iodine; lithium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile; benzene; 7: Nozaki-Hiyama-Kishi reaction;

DOI:10.1021/ol200834p

upstream raw materials:

(2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

tert-butyl(((2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentyl)oxy)diphenylsilane

(2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanal

(S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one

Downstream raw materials:

(1S,2S,3E,6S,8S,9Z)-1-(3,5-bis((triisopropylsilyl)oxy)phenyl)-10-cyclohexyl-2,6,8-trimethyldeca-3,9-diene-1,5-diol

(1S,2S,6S,8S,Z)-1-(3,5-bis((triisopropylsilyl)oxy)phenyl)-10-cyclohexyl-1-hydroxy-2,6,8-trimethyldec-9-en-5-one

(2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol

((5-((2S,3S,6S,8S,9S,11S)-8-((S)-cyclohexyliodomethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl)-1,3-phenylene)bis(oxy))bis(triisopropylsilane)