Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester

Base Information

Chemical Name:Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester
CAS No.:207680-90-8
Molecular Formula:C₃₄H₅₈O₅Si₂
Molecular Weight:603.003
Hs Code.:

Synonyms:Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester

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Chemical Property of Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester

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Technology Process of Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester

There total 12 articles about Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester 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: 99.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 160666-99-9
Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-8-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester

: 207680-90-8
Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1055/s-1998-5929

Reference yield:

: 497-03-0
2-methylbut-2-enal

: 207680-90-8
Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester

Guidance literature:: Multi-step reaction with 9 steps

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3: 96 percent / LiBH₄ / tetrahydrofuran / 24 h / 20 °C

4: 93 percent / aq. NaIO₄ / methanol / 0.5 h / 20 °C

5: 83 percent / aq. Ba(OH)2 / tetrahydrofuran / 1.) 20 deg C, 20 min, 2.) 20 deg C, 16 h

6: 98 percent / DIBAL / diethyl ether; hexane / 2 h / -40 °C

7: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

9: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; barium dihydroxide; sodium periodate; lithium borohydride; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1055/s-1998-5929

Reference yield:

: 160666-96-6
(2R,3S,4E)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-4-hexenal

: 207680-90-8
Benzoic acid (5E,9E)-(1S,3R,4R,7S,8S)-4,8-bis-(tert-butyl-dimethyl-silanyloxy)-1,3,7,9-tetramethyl-2-oxo-undeca-5,9-dienyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / aq. Ba(OH)2 / tetrahydrofuran / 1.) 20 deg C, 20 min, 2.) 20 deg C, 16 h

2: 98 percent / DIBAL / diethyl ether; hexane / 2 h / -40 °C

3: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; barium dihydroxide; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1055/s-1998-5929