(13S)-9-cis-4-oxo-13,14-dihydroretinoic acid

Base Information

Chemical Name:(13S)-9-cis-4-oxo-13,14-dihydroretinoic acid
CAS No.:1159988-03-0
Molecular Formula:C₂₀H₂₈O₃
Molecular Weight:316.441
Hs Code.:

Synonyms:

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Chemical Property of (13S)-9-cis-4-oxo-13,14-dihydroretinoic acid

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Technology Process of (13S)-9-cis-4-oxo-13,14-dihydroretinoic acid

There total 5 articles about (13S)-9-cis-4-oxo-13,14-dihydroretinoic acid 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:

: 888484-41-1
ethyl (3S)-3-methyl-4-oxobutanoate

: 1159988-03-0
(13S)-9-cis-4-oxo-13,14-dihydroretinoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.75 h / 130 °C / Inert atmosphere

2.2: 3 h / 0 - 25 °C / Inert atmosphere

3.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 5 h / 0 - 25 °C / Inert atmosphere

4.1: potassium hydroxide / methanol; water / 0.5 h / 80 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium carbonate; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.1: Julia-Kocienski olefination / 2.2: Stille coupling;
DOI:10.1016/j.tet.2011.12.056

Reference yield:

: 1357598-51-6
ethyl (S,4E,6Z)-7-iodo-3-methylocta-4,6-dienoate

: 1159988-03-0
(13S)-9-cis-4-oxo-13,14-dihydroretinoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.75 h / 130 °C / Inert atmosphere

1.2: 3 h / 0 - 25 °C / Inert atmosphere

2.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 5 h / 0 - 25 °C / Inert atmosphere

3.1: potassium hydroxide / methanol; water / 0.5 h / 80 °C / Inert atmosphere

With manganese(IV) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium carbonate; potassium hydroxide; In methanol; dichloromethane; water; toluene; 1.2: Stille coupling;
DOI:10.1016/j.tet.2011.12.056

Reference yield:

: 54998-57-1
ethyl 3-formylbutyrate

: 1159988-03-0
(13S)-9-cis-4-oxo-13,14-dihydroretinoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.75 h / 130 °C / Inert atmosphere

2.2: 3 h / 0 - 25 °C / Inert atmosphere

3.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 5 h / 0 - 25 °C / Inert atmosphere

4.1: potassium hydroxide / methanol; water / 0.5 h / 80 °C / Inert atmosphere

With manganese(IV) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium carbonate; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.2: Horner-Wadsworth-Emmons olefination / 2.2: Stille coupling;
DOI:10.1016/j.tet.2011.12.056