(S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate

Base Information

Chemical Name:(S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate
CAS No.:1332569-87-5
Molecular Formula:C₂₇H₃₅NO₆
Molecular Weight:469.578
Hs Code.:

Synonyms:(S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate

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Chemical Property of (S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate

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Technology Process of (S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate

There total 6 articles about (S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate 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: 78.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1332569-81-9
(R,E)-1-((S)-2-oxooxazolidin-4-yl)dodec-4-en-2-ynyl benzoate

: 1332569-87-5
(S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1021/ol202064j

Reference yield:

: 1332569-78-4
(R)-1-((S)-2-oxooxazolidin-4-yl)prop-2-ynyl benzoate

: 1332569-87-5
(S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere

With piperidine; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; dichloromethane; 1: Sonogashira coupling;
DOI:10.1021/ol202064j

Reference yield:

: 35042-52-5
(E)-2-penten-4-yn-1-ol

: 1332569-87-5
(S)-tert-butyl-4-((R,E)-1-(benzoyloxy)dodec-4-en-2-ynyl)-2-oxooxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -10 °C / Inert atmosphere; Molecular sieve

1.2: 24 h / -5 °C / Inert atmosphere; Molecular sieve

2.1: triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.2: 24 h / 40 °C / Inert atmosphere

3.1: piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere

With piperidine; titanium(IV) isopropylate; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethyl (2S,3S)-tartrate; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation / 3.1: Sonogashira coupling;
DOI:10.1021/ol202064j