(S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-1-one

Base Information

Chemical Name:(S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-1-one
CAS No.:1383331-13-2
Molecular Formula:C₂₁H₃₁NO₂S₂Si
Molecular Weight:421.7
Hs Code.:

Synonyms:(S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-1-one

Suppliers and Price of (S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-1-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-1-one

There total 2 articles about (S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-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: 92.0%

: 1205666-47-2
(S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-hydroxypent-4-en-1-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1383331-13-2
(S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-1-one

Guidance literature:: With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.03.010

Reference yield:

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

: 1383331-13-2
(S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-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: 0.5 h / -78 °C / Inert atmosphere

1.3: -78 - 20 °C

2.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2012.03.010

Reference yield:

: 1383331-13-2
(S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)pent-4-en-1-one

: (3S,4R,6S,9S,10R,E)-9-(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)-3-methyl-10-pentyl-4-((triethylsilyl)oxy)-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.17 h / -78 °C / Inert atmosphere

2.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.25 h / -78 - 0 °C / Inert atmosphere

3.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0.5 h / 0 °C / Inert atmosphere

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

4.2: Inert atmosphere

5.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 0.5 h / 20 °C / Inert atmosphere

5.2: 2 h / 20 °C / Inert atmosphere

6.1: Hoveyda-Grubbs catalyst first generation / toluene / 96 h / 110 °C / Inert atmosphere

With 2,6-dimethylpyridine; Hoveyda-Grubbs catalyst first generation; lithium hydroxide monohydrate; 2,4,6-trichlorobenzoyl chloride; dihydrogen peroxide; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 5.1: |Yamaguchi Lactonization / 5.2: |Yamaguchi Lactonization;
DOI:10.1021/jo501184t