(R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one

Base Information

Chemical Name:(R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one
CAS No.:917375-46-3
Molecular Formula:C₁₈H₂₃NO₃Si
Molecular Weight:329.471
Hs Code.:

Synonyms:(R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one

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Chemical Property of (R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one

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Technology Process of (R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one

There total 1 articles about (R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-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: 61.0%

: 148766-15-8
(R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one

: 1066-54-2
trimethylsilylacetylene

: 917375-46-3
(R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one

: (R)-3-((R)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one

Guidance literature:: trimethylsilylacetylene; With n-butyllithium; In hexane; toluene; at 20 ℃; for 0.5h;

With dimethylaluminum chloride; In hexane; toluene; for 0.5h; cooling;

(R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one; In hexane; toluene; for 0.5h; cooling;
DOI:10.1016/j.tet.2006.05.019

Reference yield:

: 917375-46-3
(R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one

: (S)-4-benzyl-3-[(1S,5S,7R)-7-(tert-butyldimethylsilanyloxy)-5-methyl-4-vinylcyclohept-3-enecarbonyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 82 percent / LiBH₄; MeOH / tetrahydrofuran / 8 h / 20 °C

2.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 1.5 h / cooling

3.1: Bu₂BOTf; EtN(i-Pr)2 / toluene / 1 h / cooling

3.2: 82 percent / toluene / 6 h / 20 °C

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / cooling

5.1: 82 percent / AgNO₃; 2,6-lutidine; H₂O / tetrahydrofuran; ethanol / 0.5 h / 20 °C

6.1: 59 percent / ethylene / [(1,3-Mes₂-imidazolidin-2-ylidene)(o-iPrO-benzylidene)RuCl₂] / CH₂Cl₂ / Heating

With 2,6-dimethylpyridine; methanol; lithium borohydride; oxalyl dichloride; ethene; di-n-butylboryl trifluoromethanesulfonate; water; silver nitrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; In tetrahydrofuran; ethanol; dichloromethane; toluene; 2.1: Swern oxidation;
DOI:10.1016/j.tet.2006.05.019

Reference yield:

: 917375-46-3
(R)-3-((S)-3-methyl-5-trimethylsilanyl-pent-4-ynoyl)-4-phenyl-oxazolidin-2-one

: 917375-49-6
(4S)-3-[(2S,3R,5S)-2-allyl-3-hydroxy-5-methyl-7-trimethylsilanylhept-6-ynoyl]-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / LiBH₄; MeOH / tetrahydrofuran / 8 h / 20 °C

2.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 1.5 h / cooling

3.1: Bu₂BOTf; EtN(i-Pr)2 / toluene / 1 h / cooling

3.2: 82 percent / toluene / 6 h / 20 °C

With methanol; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 2.1: Swern oxidation;
DOI:10.1016/j.tet.2006.05.019