(R)-N,2-dimethyl-N-((3S,5S,6S)-3,5,6-trimethyl-8-oxo-8-((S)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide

Base Information

Chemical Name:(R)-N,2-dimethyl-N-((3S,5S,6S)-3,5,6-trimethyl-8-oxo-8-((S)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide
CAS No.:1351186-17-8
Molecular Formula:C₂₆H₄₀N₂O₄
Molecular Weight:444.615
Hs Code.:

Synonyms:

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Chemical Property of (R)-N,2-dimethyl-N-((3S,5S,6S)-3,5,6-trimethyl-8-oxo-8-((S)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide

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Technology Process of (R)-N,2-dimethyl-N-((3S,5S,6S)-3,5,6-trimethyl-8-oxo-8-((S)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide

There total 12 articles about (R)-N,2-dimethyl-N-((3S,5S,6S)-3,5,6-trimethyl-8-oxo-8-((S)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide 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:

: C₂₅H₃₆N₂O₄

: 75-16-1
methylmagnesium bromide

: 1351186-17-8
(R)-N,2-dimethyl-N-((3S,5S,6S)-3,5,6-trimethyl-8-oxo-8-((S)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide

Guidance literature:: methylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

C₂₅H₃₆N₂O₄; In tetrahydrofuran; at -78 - -40 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1021/jo201951s

Reference yield:

: 1351186-13-4
(R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

: 1351186-17-8
(R)-N,2-dimethyl-N-((3S,5S,6S)-3,5,6-trimethyl-8-oxo-8-((S)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: lithium borohydride / methanol / 0.5 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 - 40 °C

4.1: water; triphenylphosphine / tetrahydrofuran / 12 h / 20 - 40 °C

5.1: diethyl cyanophosphonate; triethylamine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

8.2: -78 - 20 °C / Inert atmosphere

9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

9.2: 0 - 20 °C / Inert atmosphere

10.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

10.2: -78 - -40 °C / Inert atmosphere

With lithium borohydride; n-butyllithium; sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 4.1: Staudinger reaction / 8.1: Swern oxidation / 8.2: Swern oxidation / 9.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo201951s

Reference yield:

: 123444-68-8
(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

: 1351186-17-8
(R)-N,2-dimethyl-N-((3S,5S,6S)-3,5,6-trimethyl-8-oxo-8-((S)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

2.2: -78 - -40 °C / Inert atmosphere

3.1: lithium borohydride / methanol / 0.5 h / 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 - 40 °C

6.1: water; triphenylphosphine / tetrahydrofuran / 12 h / 20 - 40 °C

7.1: diethyl cyanophosphonate; triethylamine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

10.2: -78 - 20 °C / Inert atmosphere

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

11.2: 0 - 20 °C / Inert atmosphere

12.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

12.2: -78 - -40 °C / Inert atmosphere

With lithium borohydride; n-butyllithium; sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.2: Horner-Wadsworth-Emmons olefination / 6.1: Staudinger reaction / 10.1: Swern oxidation / 10.2: Swern oxidation / 11.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo201951s