Silane, (1,1-dimethylethyl)diphenyl[[(2R,4S,6E,8R)-2,4,6,8-tetramethyl-6-decen yl]oxy]-

Base Information

• Chemical Name: Silane, (1,1-dimethylethyl)diphenyl[[(2R,4S,6E,8R)-2,4,6,8-tetramethyl-6-decen yl]oxy]-
• CAS No.: 686718-85-4
• Molecular Formula: C30H46OSi
• Molecular Weight: 450.78
• Mol file: 686718-85-4.mol

Synonyms:

Chemical Property of Silane, (1,1-dimethylethyl)diphenyl[[(2R,4S,6E,8R)-2,4,6,8-tetramethyl-6-decen yl]oxy]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Silane, (1,1-dimethylethyl)diphenyl[[(2R,4S,6E,8R)-2,4,6,8-tetramethyl-6-decen yl]oxy]-

There total 17 articles about Silane, (1,1-dimethylethyl)diphenyl[[(2R,4S,6E,8R)-2,4,6,8-tetramethyl-6-decen yl]oxy]- 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: 66.0%

(R,E)-2-iodo-4-methyl-2-hexene (686718-81-0) + (2R,4S)-1-(tert-butyldiphenylsiloxy)-5-iodo-2,4-dimethylpentane (686718-83-2) → (E)-(3R,7S,9R)-10-(tert-butyldiphenylsiloxy)-3,5,7,9-tetramethyl-4-decene (686718-85-4)

Guidance literature:

(2R,4S)-1-(tert-butyldiphenylsiloxy)-5-iodo-2,4-dimethylpentane; With tert.-butyl lithium; zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.5h;

(R,E)-2-iodo-4-methyl-2-hexene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.01.156

Reference yield:

methyllithium (917-54-4) + Toluene-4-sulfonic acid (E)-(2S,6S,8R)-9-(tert-butyl-diphenyl-silanyloxy)-2,4,6,8-tetramethyl-non-3-enyl ester (273738-38-8) → (E)-(3R,7S,9R)-10-(tert-butyldiphenylsiloxy)-3,5,7,9-tetramethyl-4-decene (686718-85-4)

Guidance literature:

methyllithium; With copper(l) iodide; In diethyl ether; at -10 ℃; for 0.5h;

Toluene-4-sulfonic acid (E)-(2S,6S,8R)-9-(tert-butyl-diphenyl-silanyloxy)-2,4,6,8-tetramethyl-non-3-enyl ester; In diethyl ether; at 20 ℃; for 13h;

DOI:10.1002/anie.200454192

Reference yield:

(S)-(((4,4-dibromo-2-methylbut-3-en-1-yl)oxy)methyl)benzene (246219-82-9) → (E)-(3R,7S,9R)-10-(tert-butyldiphenylsiloxy)-3,5,7,9-tetramethyl-4-decene (686718-85-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 342 mg / hexane; tetrahydrofuran / 1 h / 0 °C

2.1: Cp₂ZrHCl / benzene / 0.5 h / 40 °C

2.2: I₂ / benzene / 0.5 h / 20 °C

2.3: 188 mg / tetrakis(triphenylphosphine)palladium / diethyl ether; pentane; tetrahydrofuran / 13 h / 20 °C

3.1: 90 percent / lithium 4,4'-di-tert-butylbiphenylide / tetrahydrofuran / 0.08 h / -78 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

5.1: CuI / diethyl ether / 0.5 h / -10 °C

5.2: 49.2 mg / diethyl ether / 13 h / 20 °C

With dmap; copper(l) iodide; Schwartz's reagent; n-butyllithium; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 2.3: Negishi coupling;

DOI:10.1055/s-2007-965893

upstream raw materials:

(R,E)-2-iodo-4-methyl-2-hexene

(2R,4S)-1-(tert-butyldiphenylsiloxy)-5-iodo-2,4-dimethylpentane

methyllithium

Toluene-4-sulfonic acid (E)-(2S,6S,8R)-9-(tert-butyl-diphenyl-silanyloxy)-2,4,6,8-tetramethyl-non-3-enyl ester

Refernces

• 1、 Inoue, Munenori,Yokota, Wakako,Katoh, Tadashi. "Enantioselective total synthesis of (+)-scyphostatin, a potent and specific inhibitor of neutral sphingomyelinase". . p. 622 - 637. Retrieved 2008/01/04.