(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

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Chemical Name:(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one
CAS No.:1453081-88-3
Molecular Formula:C₂₂H₂₉NO₆
Molecular Weight:403.475
Hs Code.:

Synonyms:(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

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Chemical Property of (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

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Technology Process of (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

There total 4 articles about (4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-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: 85.0%

: 1453081-86-1
(4R,5S)-3-(2-bromo-2-methylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

: 116669-78-4
(4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde

: 1453081-88-3
(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -78 ℃; for 1h; Reagent/catalyst; Temperature; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201300148

Reference yield:

: 638211-38-8
(4R,5S)-5-methyl-4-phenyloxazolidin-2-one

: 1453081-88-3
(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 2 h / -40 - 0 °C / Inert atmosphere

2.1: samarium diiodide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

With samarium diiodide; sodium hydride; In tetrahydrofuran; 2.1: |Reformatsky Reaction;
DOI:10.1002/ejoc.201300148

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 1453081-88-3
(4R,5S)-3-((S)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropanoyl)-5-methyl-4-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 14 h / 0 - 20 °C / Inert atmosphere

2.1: water; sodium periodate / dichloromethane / 2 h / 20 °C / Cooling

3.1: samarium diiodide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

With sodium periodate; samarium diiodide; potassium tert-butylate; water; In tetrahydrofuran; dichloromethane; 1.2: |Wittig Olefination / 3.1: |Reformatsky Reaction;
DOI:10.1002/ejoc.201300148