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

Base Information

• Chemical Name: (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-10-phenyl-2,4,6,8-tetramethyl-2,6-decadienal
• CAS No.: 186895-61-4
• Molecular Formula: C₂₆H₄₂O₂Si
• Molecular Weight: 414.704
• Mol file: 186895-61-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-10-phenyl-2,4,6,8-tetramethyl-2,6-decadienal 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: 92.0%

(2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-2,4,6,8-tetramethyl-10-phenyl-2,6-decadienol (186895-60-3) → (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-10-phenyl-2,4,6,8-tetramethyl-2,6-decadienal (186895-61-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 25 ℃;

DOI:10.1055/s-2002-19806

Reference yield: 80.0%

(2S,3R,4E,6S)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-8-phenyl-4-octanal (186895-58-9) + 2-triethylsilylpropionaldehyde N-cyclohexylimine → (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-10-phenyl-2,4,6,8-tetramethyl-2,6-decadienal (186895-61-4)

Guidance literature:

(2S,3R,4E,6S)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-8-phenyl-4-octanal; 2-triethylsilylpropionaldehyde N-cyclohexylimine; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -20 ℃; for 1h;

With trifluoroacetic acid; In tetrahydrofuran; at 0 ℃; for 1h;

In tetrahydrofuran; water; at 0 ℃; for 12h;

DOI:10.1021/ol048905v

Reference yield:

(3R,4R,5E,7S)-4-(tert-butyldimethylsilyloxy)-3,5,7-trimethyl-9-phenyl-1,5-nonadiene (186895-56-7) → (2E,4R,5R,6E,8S)-5-(tert-butyldimethylsilyloxy)-10-phenyl-2,4,6,8-tetramethyl-2,6-decadienal (186895-61-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / AD-mix / 2-methyl-propan-2-ol; H₂O

2: 99 percent / Pb(OAc)4 / CH₂Cl₂ / 0 °C

3: 95 percent / benzene / 25 °C

4: 97 percent / iBu₂AlH / tetrahydrofuran / -40 °C

5: 80 percent / TPAP; NMO / CH₂Cl₂ / 0 °C

With lead(IV) acetate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1021/ol990944x

upstream raw materials:

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

(2S,3R,4E,6S)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-8-phenyl-4-octanal

(3R,4R,5E,7S)-4-(tert-butyldimethylsilyloxy)-3,5,7-trimethyl-9-phenyl-1,5-nonadiene

(2RS,3R,4R,5E,7S)-4-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3,5,7-trimethyl-9-phenyl-5-nonene

Downstream raw materials:

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

(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

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