(2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-phenylselanyl-nona-2,8-dienoic acid ethyl ester

Base Information

• Chemical Name: (2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-phenylselanyl-nona-2,8-dienoic acid ethyl ester
• CAS No.: 138325-25-4
• Molecular Formula: C₃₅H₅₃ClO₄SSeSi₂
• Molecular Weight: 740.453
• Mol file: 138325-25-4.mol

Synonyms:

Chemical Property of (2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-phenylselanyl-nona-2,8-dienoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-phenylselanyl-nona-2,8-dienoic acid ethyl ester

There total 3 articles about (2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-phenylselanyl-nona-2,8-dienoic acid ethyl 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: 64.0%

sodium phenylselenide (23974-72-3) + (2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-(diphenoxy-phosphoryloxy)-nona-2,8-dienoic acid ethyl ester (138325-24-3,138347-79-2) → (E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-oxo-non-8-enoic acid ethyl ester (138325-29-8) + (2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-phenylselanyl-nona-2,8-dienoic acid ethyl ester (138325-25-4,138325-28-7)

Guidance literature:

In tetrahydrofuran; for 1.5h;

DOI:10.1039/P19910002894

Reference yield:

(E)-(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-chloro-phenylsulfanyl)-hept-6-enoic acid (138325-26-5) → (2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-phenylselanyl-nona-2,8-dienoic acid ethyl ester (138325-25-4,138325-28-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / Carbonyl diimidazolide, magnesium ethoxide

2: 98 percent / NaOH, Bu₄NHSO₄ / CH₂Cl₂

3: 29 percent / tetrahydrofuran / 1.5 h

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; magnesium ethylate; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane;

DOI:10.1039/P19910002894

Reference yield:

(E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-oxo-non-8-enoic acid ethyl ester (138325-29-8) → (2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-phenylselanyl-nona-2,8-dienoic acid ethyl ester (138325-25-4,138325-28-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaOH, Bu₄NHSO₄ / CH₂Cl₂

2: 29 percent / tetrahydrofuran / 1.5 h

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; dichloromethane;

DOI:10.1039/P19910002894

upstream raw materials:

sodium phenylselenide

(2Z,8E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-(diphenoxy-phosphoryloxy)-nona-2,8-dienoic acid ethyl ester

(E)-(3S,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-chloro-phenylsulfanyl)-hept-6-enoic acid

(E)-(5S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-chloro-phenylsulfanyl)-3-oxo-non-8-enoic acid ethyl ester

Downstream raw materials:

Ethyl <3S^*-(1E,3α,5β)>-<3,5-Bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexyllidene>acetate

[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-acetic acid ethyl ester

[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(4-chloro-phenylsulfanylmethyl)-cyclohex-(E)-ylidene]-acetic acid ethyl ester