(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one

Base Information

Chemical Name:(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one
CAS No.:1360109-96-1
Molecular Formula:C₃₀H₄₃NO₅S₂Si
Molecular Weight:589.893
Hs Code.:

Synonyms:(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one

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Chemical Property of (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one

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Technology Process of (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one

There total 3 articles about (S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-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: 93.0%

: 1360109-95-0
(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-5-(3,4,5-trimethoxyphenyl)pentan-1-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 1360109-96-1
(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.11.010

Reference yield:

: 86-81-7
3,4,5-trimethoxy-benzaldehyde

: 1360109-96-1
(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: benzene / 4 h / Reflux; Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux

3.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.08 h / -78 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; titanium tetrachloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; benzene; 1.1: Wittig reaction / 4.2: Crimmins aldol reaction;
DOI:10.1016/j.tetasy.2011.11.010

Reference yield:

: 121667-78-5
3-(3',4',5'-trimethoxyphenyl)propanal

: 1360109-96-1
(S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-(tert-butyldimethylsilyloxy)-5-(3,4,5-trimethoxyphenyl)pentan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.08 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.2: Crimmins aldol reaction;
DOI:10.1016/j.tetasy.2011.11.010