(2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)pentan-1-one

Base Information

Chemical Name:(2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)pentan-1-one
CAS No.:890016-99-6
Molecular Formula:C₂₅H₄₁NO₂S₂Si
Molecular Weight:479.824
Hs Code.:

Synonyms:(2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)pentan-1-one

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Chemical Property of (2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)pentan-1-one

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Technology Process of (2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)pentan-1-one

There total 2 articles about (2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)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:

: 890016-82-7
(2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 890016-99-6
(2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)pentan-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/ol0607241

Reference yield:

: 863324-53-2
(R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one

: 890016-99-6
(2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)pentan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: TiCl₄; ethyldiisopropylamine / CH₂Cl₂ / 0.08 h / 0 °C

2: 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

With 2,6-dimethylpyridine; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ol0607241

Reference yield:

: 890016-99-6
(2S,3R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-2-methyl-3-(triisopropylsilyloxy)pentan-1-one

: 890016-95-2
(2S,4R)-4-((4S,5S,6R)-6-((2R,3R)-3-(tert-butyldimethylsilyloxy)pentan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2-methylpentanal

Guidance literature:: Multi-step reaction with 14 steps

1.1: DIBAL / CH₂Cl₂; hexane / -78 °C

2.1: TiCl₄; (-)-sparteine / CH₂Cl₂; 1-methyl-pyrrolidin-2-one / -20 - 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

4.1: DIBAL / CH₂Cl₂; hexane / -78 °C

5.1: TiCl₄; ethyldiisopropylamine / CH₂Cl₂; 1-methyl-pyrrolidin-2-one / 0 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

7.1: LiBH₄ / methanol; tetrahydrofuran / 20 °C

8.1: I₂; imidazole; PPh₃ / CH₂Cl₂ / 48 h / 20 °C

9.1: p-TSA / CH₂Cl₂; methanol

10.1: CSA / CH₂Cl₂; methanol

11.1: 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

12.1: LiCl; lithium diisopropylamide / tetrahydrofuran / 0.67 h / -78 - 20 °C

12.2: tetrahydrofuran / 0 °C

13.1: lithium diisopropylamide; NH₃*BH₃ / tetrahydrofuran / -78 - 20 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With 1H-imidazole; 2,6-dimethylpyridine; lithium borohydride; ammonia borane; camphor-10-sulfonic acid; iodine; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; (-)-sparteine; lithium diisopropyl amide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; hexane; dichloromethane; 12.2: Myers alkylation;
DOI:10.1021/ol0607241