(1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene

Base Information

• Chemical Name: (1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene
• CAS No.: 186895-62-5
• Molecular Formula: C₂₇H₄₃IOSi
• Molecular Weight: 538.628
• Mol file: 186895-62-5.mol

Synonyms:(1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene

Chemical Property of (1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene

There total 26 articles about (1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene 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: 86.0%

(3E,5R,6R,7E,9S)-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-3,7-undecadien-1-yne (770711-49-4) → (1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene (186895-62-5)

Guidance literature:

(3E,5R,6R,7E,9S)-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-3,7-undecadien-1-yne; With Schwartz's reagent; In tetrahydrofuran; at 23 ℃; for 4h;

With iodine; at 0 - 23 ℃; for 2h;

DOI:10.1021/ol048905v

Reference yield:

iodoform (75-47-8) + (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-10-phenyl-2,4,6,8-tetramethyl-2,6-decadienal (186895-61-4) → (1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene (186895-62-5) + tert-Butyl-[(3E,5Z)-(1R,2R)-1-((E)-(S)-1,3-dimethyl-5-phenyl-pent-1-enyl)-6-iodo-2,4-dimethyl-hexa-3,5-dienyloxy]-dimethyl-silane

Guidance literature:

With chromium dichloride; In tetrahydrofuran; at 0 ℃; for 3h; Yield given. Yields of byproduct given;

DOI:10.1021/ja972603p

Reference yield:

(2S,3R,4E,6S)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-8-phenyl-4-octanal (186895-58-9) → (1E,3E,5R,6R,7E,9S)-1-iodo-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-1,3,7-undecatriene (186895-62-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Ph₃P; Zn / CH₂Cl₂ / 6 h / 23 °C

2.1: nBuLi; ZnBr₂ / tetrahydrofuran; hexane / 0.92 h / -78 - -23 °C

2.2: 75 percent / DIBAH / tetrahydrofuran; hexane / 12 h / 23 °C

3.1: 100 percent / Pd(tBu₃P)2 / tetrahydrofuran; toluene / 1 h / 23 °C

4.1: 98 percent / K₂CO₃ / methanol / 3 h / 23 °C

5.1: HZrCp₂Cl / tetrahydrofuran / 4 h / 23 °C

5.2: 86 percent / I₂ / 2 h / 0 - 23 °C

With Schwartz's reagent; n-butyllithium; bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; triphenylphosphine; zinc dibromide; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1021/ol048905v

upstream raw materials:

iodoform

(2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-10-phenyl-2,4,6,8-tetramethyl-2,6-decadienal

(3E,5R,6R,7E,9S)-3,5,7,9-tetramethyl-6-(t-butyldimethylsilyloxy)-11-phenyl-3,7-undecadien-1-yne

(S)-4-methyl-6-phenyl-2-hexyne

Downstream raw materials:

(2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid

ethyl (2E,4E,8E,10E,12R,13R,14E,16S)-2,10,12,14,16-pentamethyl-13-hydroxy-18-phenyl-2,4,8,10,14-octadecapentaen-6-ynoate

Phenalamid A₃

phenalamide A₁