(3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one

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Chemical Name:(3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one
CAS No.:1374348-42-1
Molecular Formula:C₂₉H₃₉NO₃S₂Si
Molecular Weight:541.851
Hs Code.:

Synonyms:(3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one

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Chemical Property of (3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one

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Technology Process of (3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one

There total 1 articles about (3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-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:

: 14371-10-9
(E)-3-phenylpropenal

: 1374348-42-1
(3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: titanium tetrachloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 0.17 h / 0 °C / Inert atmosphere

1.3: 1 h / -78 °C / Inert atmosphere

2.1: dichloromethane / 1 h

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

4.1: titanium tetrachloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

4.2: 0.17 h / 0 °C / Inert atmosphere

4.3: 1 h / -78 °C / Inert atmosphere

With titanium tetrachloride; diisobutylaluminium hydride; In dichloromethane; toluene;
DOI:10.1016/j.tetlet.2012.02.073

Reference yield:

: 1374348-42-1
(3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one

: 1374348-52-3
C₁₉H₃₀O₃Si

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2012.02.073

Reference yield:

: 1374348-42-1
(3S,5S,E)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-7-phenylhept-6-en-1-one

: 91327-34-3
(R)-6-((S,E)-2-hydroxy-4-phenylbut-3-en-1-yl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C

2.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C

2.2: -78 °C

3.1: camphor-10-sulfonic acid / benzene / 1 h / 20 °C

4.1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; camphor-10-sulfonic acid; water; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene; benzene; 2.2: Still-Gennari reaction;
DOI:10.1016/j.tetlet.2012.02.073