(3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal

Base Information

Chemical Name:(3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal
CAS No.:937800-21-0
Molecular Formula:C₃₄H₅₀O₃Si₂
Molecular Weight:562.94
Hs Code.:

Synonyms:(3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal

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Chemical Property of (3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal

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Technology Process of (3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal

There total 13 articles about (3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal 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: 32.0%

: 937800-19-6
(5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene

: 937800-21-0
(3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal

Guidance literature:: (5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 1.5h; pH=8;

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.333333h; Further stages.;
DOI:10.1021/jo0701942

Reference yield:

: 624727-26-0
ethyl 5-[(4-methoxybenzyl)oxy]-3-oxopentanoate

: 937800-21-0
(3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal

Guidance literature:: Multi-step reaction with 12 steps

1.1: 86 percent / (R)-BINAP; hydrogen / [RuCl₂(C₆H₆)]2 / dimethylformamide; ethanol / 62 h / 20 °C / 15001.5 Torr

2.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: diisobutylaluminium hydride / CH₂Cl₂; hexane / -78 - 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: tetrahydrofuran; hexane / -78 - 20 °C

5.1: 8.4 g / K₂CO₃ / methanol / 0 - 20 °C

6.1: propionic acid / 7 h / 110 °C

7.1: 99 mg / Al₂O₃ / toluene / 0.25 h / 100 °C

8.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 0.08 h / -78 °C

9.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 °C

10.1: 85 percent / AgOTf; (S)-Tol-BINAP / tetrahydrofuran / 20 h / -20 °C

11.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C

12.1: DDQ / CH₂Cl₂; various solvent(s) / 1.5 h / 20 °C / pH 8

12.2: 32 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; aluminum oxide; n-butyllithium; oxalyl dichloride; hydrogen; silver trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; propionic acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dichloro(benzene)ruthenium(II) dimer; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: asymmetric Noyori hydrogenation / 9.1: Swern oxidation;
DOI:10.1021/jo0701942

Reference yield:

: 937800-24-3
C₂₄H₄₂O₄Si₂

: 937800-21-0
(3S,5Z,7E,9S)-3-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)dodeca-5,7,11-trienal

Guidance literature:: Multi-step reaction with 8 steps

1.1: 8.4 g / K₂CO₃ / methanol / 0 - 20 °C

2.1: propionic acid / 7 h / 110 °C

3.1: 99 mg / Al₂O₃ / toluene / 0.25 h / 100 °C

4.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 0.08 h / -78 °C

5.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 °C

6.1: 85 percent / AgOTf; (S)-Tol-BINAP / tetrahydrofuran / 20 h / -20 °C

7.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C

8.1: DDQ / CH₂Cl₂; various solvent(s) / 1.5 h / 20 °C / pH 8

8.2: 32 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

With 1H-imidazole; aluminum oxide; oxalyl dichloride; silver trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; propionic acid; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Swern oxidation;
DOI:10.1021/jo0701942