(S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Base Information

Chemical Name:(S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one
CAS No.:1373353-23-1
Molecular Formula:C₂₀H₂₂N₄O₄
Molecular Weight:382.419
Hs Code.:

Synonyms:(S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

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Chemical Property of (S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

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Technology Process of (S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

There total 4 articles about (S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-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: 76.0%

: 1373353-19-5
(S)-3-((S)-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

: 1373353-23-1
(S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Guidance literature:: (S)-3-((S)-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one; With potassium hexamethylsilazane; sodium hydride; In tetrahydrofuran; mineral oil; at -78 ℃; for 0.5h; Inert atmosphere;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; at -78 ℃; for 0.25h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/cjoc.201180489

Reference yield:

: 539-47-9,15690-24-1
3-(fur-2-yl)crotonic acid

: 1373353-23-1
(S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran / 1.5 h / -78 - 0 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere

3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / -78 - 0 °C

3.2: 3.25 h / -78 - 20 °C / Inert atmosphere

4.1: potassium hexamethylsilazane; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.25 h / -78 °C / Inert atmosphere

With copper(I) bromide dimethylsulfide complex; potassium hexamethylsilazane; sodium hydride; triethylamine; In tetrahydrofuran; mineral oil; 3.1: 1,4-Michael addition / 3.2: 1,4-Michael addition;
DOI:10.1002/cjoc.201180489

Reference yield:

: 1373353-17-3
(S,E)-3-(3-(furan-2-yl)acryloyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

: 1373353-23-1
(S)-3-((2S,3S)-2-azido-3-(furan-2-yl)pentanoyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / -78 - 0 °C

1.2: 3.25 h / -78 - 20 °C / Inert atmosphere

2.1: potassium hexamethylsilazane; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.25 h / -78 °C / Inert atmosphere

With copper(I) bromide dimethylsulfide complex; potassium hexamethylsilazane; sodium hydride; In tetrahydrofuran; mineral oil; 1.1: 1,4-Michael addition / 1.2: 1,4-Michael addition;
DOI:10.1002/cjoc.201180489