benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate

Base Information

Chemical Name:benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate
CAS No.:1364375-94-9
Molecular Formula:C₄₆H₇₀N₄O₁₀
Molecular Weight:839.083
Hs Code.:

Synonyms:benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate

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Chemical Property of benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate

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Technology Process of benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate

There total 10 articles about benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate 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: 65.0%

: 1364376-27-1
(S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoic acid

: 100-39-0
benzyl bromide

: 1364375-94-9
benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate

Guidance literature:: With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide; at -20 - 20 ℃; for 16h; Inert atmosphere;
DOI:10.1039/c2cc17958j

Reference yield:

: 626-64-2,157061-69-3
pyridin-4-ol

: 1364375-94-9
benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium acetate; sodium hydroxide / water / Reflux; Inert atmosphere

1.2: Inert atmosphere; Reflux

2.1: phosphorus tribromide / ethyl acetate / 4.5 h / 145 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; diethyl ether; water / 0.08 h / 20 °C / Inert atmosphere

3.2: 24 h / Inert atmosphere; Reflux

4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 30 h / 45 °C / Inert atmosphere

5.1: copper(l) iodide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8.5 h / 20 °C / Inert atmosphere

6.1: hydrogen; palladium / methanol / 96 h / 20 °C

7.1: tetra-(n-butyl)ammonium iodide; caesium carbonate / N,N-dimethyl-formamide / 16 h / -20 - 20 °C / Inert atmosphere

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trifuran-2-yl-phosphane; hydrogen; sodium acetate; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; caesium carbonate; palladium; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; 4.1: Sonogashira coupling / 5.1: Sonogashira coupling;
DOI:10.1039/c2cc17958j

Reference yield:

: 1364375-86-9
benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-5-(trimethylsilyl)pent-4-ynoate

: 1364375-94-9
benzyl (S)-2-(tert-butoxycarbonyl)amino-5-[3,5-bis(2-{[(S)-2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl]ethyl})pyridin-4-yl]pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran; ethanol / 1.5 h / 0 °C / Inert atmosphere

2: copper(l) iodide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8.5 h / 20 °C / Inert atmosphere

3: hydrogen; palladium / methanol / 96 h / 20 °C

4: tetra-(n-butyl)ammonium iodide; caesium carbonate / N,N-dimethyl-formamide / 16 h / -20 - 20 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; trifuran-2-yl-phosphane; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; caesium carbonate; palladium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; 2: Sonogashira coupling;
DOI:10.1039/c2cc17958j