(3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one

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Chemical Name:(3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one
CAS No.:1445989-91-2
Molecular Formula:C₂₈H₄₃NO₃S₂Si
Molecular Weight:533.872
Hs Code.:

Synonyms:(3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one

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Chemical Property of (3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one

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Technology Process of (3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one

There total 7 articles about (3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-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: 60.0%

: 1445989-89-8
(R,E)-3-(tert-butyldimethylsilyloxy)-6-methylnona-6,8-dienal

: 790661-41-5
(S)-1-(4-benzyl-2-thioxothiazolidin-3-yl)ethan-1-one

: 1445989-90-1
(3S,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one

: 1445989-91-2
(3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one

Guidance literature:: (S)-1-(4-benzyl-2-thioxothiazolidin-3-yl)ethan-1-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -40 ℃; for 2h; Inert atmosphere;

(R,E)-3-(tert-butyldimethylsilyloxy)-6-methylnona-6,8-dienal; In dichloromethane; at -78 ℃; for 0.333333h; Inert atmosphere;
DOI:10.1021/jo400929m

Reference yield:

: 1445989-88-7
C₂₆H₃₉NO₂S₂Si

: 1445989-91-2
(3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / toluene; dichloromethane / 0.08 h / -78 °C / Inert atmosphere

2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -40 °C / Inert atmosphere

2.2: 0.33 h / -78 °C / Inert atmosphere

With titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 2.2: |Aldol Addition;
DOI:10.1021/jo400929m

Reference yield:

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

: 1445989-91-2
(3R,5R,E)-1-[(S)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(tert-butyldimethylsilyloxy)-3-hydroxy-8-methylundeca-8,10-dien-1-one

Guidance literature:: Multi-step reaction with 6 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

4.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / toluene; dichloromethane / 0.08 h / -78 °C / Inert atmosphere

6.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -40 °C / Inert atmosphere

6.2: 0.33 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 1.1: |Kumada Cross-Coupling / 2.1: |Swern Oxidation / 3.2: |Aldol Addition / 6.2: |Aldol Addition;
DOI:10.1021/jo400929m