(S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one

Base Information

Chemical Name:(S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one
CAS No.:1445989-81-0
Molecular Formula:C₂₀H₂₅NO₂S₂
Molecular Weight:375.556
Hs Code.:

Synonyms:(S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one

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Chemical Property of (S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one

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Technology Process of (S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one

There total 6 articles about (S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one 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: 75.0%

: 911040-42-1
1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone

: 139026-03-2
(E)-4-Methyl-4,6-heptadienal

: 1445989-81-0
(S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one

: 1445989-80-9
(3R,6E)-1-((4R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-6-methylnona-6,8-dien-1-one

Guidance literature:: With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 7h; stereoselective reaction;
DOI:10.1016/j.tetlet.2013.06.071

Reference yield:

: 5390-04-5
pent-1-yn-5-ol

: 1445989-81-0
(S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: zirconocene dichloride / 1,2-dichloro-ethane / 24 h / 0 - 20 °C / Inert atmosphere

1.2: 0.5 h / 0 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 3 h / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere

4.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -40 °C / Inert atmosphere

4.2: 0.33 h / -78 - -40 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1,2-dichloro-ethane; toluene; 1.1: |Negishi Coupling / 2.1: |Kumada Cross-Coupling / 3.1: |Swern Oxidation / 4.2: |Aldol Addition;
DOI:10.1021/jo400929m

Reference yield:

: 104846-46-0
(4E)-5-iodo-4-methylpent-4-en-1-ol

: 1445989-81-0
(S,E)-1-{(R)-4-benzyl-2-thioxothiazolidin-3-yl}-3-hydroxy-6-methylnona-6,8-dien-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 3 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere

3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -40 °C / Inert atmosphere

3.2: 0.33 h / -78 - -40 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 1.1: |Kumada Cross-Coupling / 2.1: |Swern Oxidation / 3.2: |Aldol Addition;
DOI:10.1021/jo400929m