(4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

Base Information

Chemical Name:(4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone
CAS No.:1361955-27-2
Molecular Formula:C₁₉H₂₃NO₃S₂
Molecular Weight:377.529
Hs Code.:

Synonyms:(4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

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Chemical Property of (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

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Technology Process of (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

There total 3 articles about (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone 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:

: 1361955-15-8
C₁₃H₁₃NO₃S₂

: 513-81-5
2,3-dimethyl-buta-1,3-diene

: (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

: 1361955-27-2
(4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

Guidance literature:: With copper(II) bis(trifluoromethanesulfonate); 2,2′-methylene bis[(4R,5S)-4,5-diphenyl-2-oxazoline]; In dichloromethane; at 20 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tet.2012.01.039

Reference yield:

: 104324-16-5
(4S)-(+)-3-(chloroacetyl)-4-(phenylmethyl)-2-oxazolidinone

: (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

: 1361955-27-2
(4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 2 steps

1.1: sulfur; triethylamine / acetonitrile / 2.5 h / 20 °C

1.2: 15 h / 20 °C

2.1: copper(II) bis(trifluoromethanesulfonate); 2,2′-methylene bis[(4R,5S)-4,5-diphenyl-2-oxazoline] / dichloromethane / 20 °C

With copper(II) bis(trifluoromethanesulfonate); sulfur; triethylamine; 2,2′-methylene bis[(4R,5S)-4,5-diphenyl-2-oxazoline]; In dichloromethane; acetonitrile; 2.1: Diels-Alder reaction;
DOI:10.1016/j.tet.2012.01.039

Reference yield:

: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

: (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

: 1361955-27-2
(4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: sulfur; triethylamine / acetonitrile / 2.5 h / 20 °C

2.2: 15 h / 20 °C

3.1: copper(II) bis(trifluoromethanesulfonate); 2,2′-methylene bis[(4R,5S)-4,5-diphenyl-2-oxazoline] / dichloromethane / 20 °C

With copper(II) bis(trifluoromethanesulfonate); sodium hydride; sulfur; triethylamine; 2,2′-methylene bis[(4R,5S)-4,5-diphenyl-2-oxazoline]; In tetrahydrofuran; dichloromethane; acetonitrile; 3.1: Diels-Alder reaction;
DOI:10.1016/j.tet.2012.01.039