(2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-en-1-one

Base Information

Chemical Name:(2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-en-1-one
CAS No.:1395342-47-8
Molecular Formula:C₂₃H₃₅NO₂S₂Si
Molecular Weight:449.754
Hs Code.:

Synonyms:(2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-en-1-one

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Chemical Property of (2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-en-1-one

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Technology Process of (2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-en-1-one

There total 1 articles about (2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-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: 83.0%

: 1395342-32-1
(2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylhex-5-en-1-one

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 1395342-47-8
(2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-en-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃; Inert atmosphere;
DOI:10.1055/s-0031-1290670

Reference yield:

: 1395342-47-8
(2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-en-1-one

: 1395342-48-9
(4R,5R,11R,12S,E)-4,12-bis((triethylsilyl)oxy)-5,11-dimethyl-12-(4-bromophenyl)-1,6-dodecadiene-8-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

2.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With diisobutylaluminium hydride; barium(II) hydroxide; In tetrahydrofuran; hexane; dichloromethane; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1290670

Reference yield:

: 1395342-47-8
(2S,3R)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-((triethylsilyl)oxy)hex-5-en-1-one

: 1395342-33-2
(4R,5R,11R,12S)-4,12-bis((triethylsilyl)oxy)-5,11-dimethyl-12-(4-bromophenyl)-1-dodecene-8-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

2.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; methyllithium; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -50 °C / Inert atmosphere

3.2: 1 h / -50 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; methyllithium; diisobutylaluminium hydride; barium(II) hydroxide; In tetrahydrofuran; hexane; dichloromethane; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1290670