(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
Hs Code.:

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

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

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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%

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

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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 25 ℃;
DOI:10.1055/s-2002-19806

Reference yield: 80.0%

: 186895-58-9
(2S,3R,4E,6S)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethyl-8-phenyl-4-octanal

: 2-triethylsilylpropionaldehyde N-cyclohexylimine

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

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:

: 186895-56-7
(3R,4R,5E,7S)-4-(tert-butyldimethylsilyloxy)-3,5,7-trimethyl-9-phenyl-1,5-nonadiene

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

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