1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-1-one

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Chemical Name:1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-1-one
CAS No.:937207-96-0
Molecular Formula:C₃₁H₄₅NO₃SSi
Molecular Weight:539.855
Hs Code.:

1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-methyl-6-<i>p</i>-tolyl-heptan-1-one

Synonyms:1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-1-one

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Chemical Property of 1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-1-one

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Technology Process of 1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-1-one

There total 9 articles about 1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-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: 97.0%

: 937207-95-9
1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-6-p-tolyl-heptan-1-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 937207-96-0
1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2007.02.103

Reference yield:

: 937207-94-8
4-benzyl-3-(2-p-tolyl-propionyl)-oxazolidin-2-one

: 937207-96-0
1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

2: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

3: 1.77 g / CH₂Cl₂ / 12 h / 20 °C

4: 99 percent / H₂ / Pd/C / ethyl acetate / 3 h

5: 78 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

6: 93 percent / TiCl₄; N,N-diisopropylethylamine / CH₂Cl₂ / 1.5 h / -78 °C

7: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; 2: Swern oxidation / 3: Wittig olefination / 6: Crimmins protocol;
DOI:10.1016/j.tetlet.2007.02.103

Reference yield:

: 622-47-9
4-tolylacetic acid

: 937207-96-0
1-(4-benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-p-tolyl-heptan-1-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 82 percent / Et₃N; pivaloyl chloride / tetrahydrofuran / -20 - 20 °C

2.1: LDA / tetrahydrofuran / 1 h / -78 °C

2.2: 56 percent / HMPA / tetrahydrofuran / 2 h / -30 °C

3.1: 95 percent / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

4.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

5.1: 1.77 g / CH₂Cl₂ / 12 h / 20 °C

6.1: 99 percent / H₂ / Pd/C / ethyl acetate / 3 h

7.1: 78 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

8.1: 93 percent / TiCl₄; N,N-diisopropylethylamine / CH₂Cl₂ / 1.5 h / -78 °C

9.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; hydrogen; pivaloyl chloride; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; 4.1: Swern oxidation / 5.1: Wittig olefination / 8.1: Crimmins protocol;
DOI:10.1016/j.tetlet.2007.02.103