[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone

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Chemical Name:[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone
CAS No.:350987-73-4
Molecular Formula:C₂₂H₃₁NO₃SSi
Molecular Weight:417.645
Hs Code.:

Synonyms:[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone

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Chemical Property of [(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone

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Technology Process of [(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone

There total 4 articles about [(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone 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: 91.0%

: 350987-71-2
(2R,3S)-1-[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-3-(tert-butyldimethylsilanyloxy)-2-vinylhex-5-en-1-one

: 350987-73-4
[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; for 2.5h; Heating;
DOI:10.1021/jo015568k

Reference yield:

: (R)-4-benzyl-2-oxazolidinethione

: 350987-73-4
[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

2.1: titanium tetrachloride; (-)-sparteine / CH₂Cl₂ / 2 h / -78 °C

2.2: 75 percent / CH₂Cl₂ / -78 - 0 °C

3.1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

4.1: 91 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 2.5 h / Heating

With 2,6-dimethylpyridine; titanium tetrachloride; triethylamine; (-)-sparteine; Grubbs catalyst first generation; In dichloromethane; 2.2: Evans aldol reaction;
DOI:10.1021/jo015568k

Reference yield:

: 350987-65-4
1-[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]but-2-en-1-one

: 350987-73-4
[(4R)-4-benzyl-2-thioxooxazolidin-3-yl]-[(1R,5S)-5-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]methanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: titanium tetrachloride; (-)-sparteine / CH₂Cl₂ / 2 h / -78 °C

1.2: 75 percent / CH₂Cl₂ / -78 - 0 °C

2.1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

3.1: 91 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / 2.5 h / Heating

With 2,6-dimethylpyridine; titanium tetrachloride; (-)-sparteine; Grubbs catalyst first generation; In dichloromethane; 1.2: Evans aldol reaction;
DOI:10.1021/jo015568k