(2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

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Chemical Name:(2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate
CAS No.:1448429-19-3
Molecular Formula:C₂₁H₂₂N₆O₅S
Molecular Weight:470.509
Hs Code.:

Synonyms:(2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

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Chemical Property of (2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

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Technology Process of (2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

There total 7 articles about (2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-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: 92.6%

: 1448428-90-7
(2S,3S)-ethyl 3-((S)-1-oxo-1-(prop-2-ynylamino)-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

: 622-37-7
Phenyl azide

: 1448429-19-3
(2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

Guidance literature:: With copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; In ethanol; water; tert-butyl alcohol; at 25 ℃; for 12h;
DOI:10.1021/jm4006719

Reference yield:

: 63734-73-6,66647-16-3,68521-71-1,89886-73-7,93061-20-2,149884-11-7
ethyl (2S,3S)-2,3-epoxysuccinate

: 1448429-19-3
(2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere

2: copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine / ethanol; water; tert-butyl alcohol / 12 h / 25 °C

With benzotriazol-1-ol; copper(II) sulfate; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; In ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: |Huisgen Cycloaddition;
DOI:10.1021/jm4006719

Reference yield:

: 13811-71-7
diethyl (2S,3S)-tartrate

: 1448429-19-3
(2S,3S)-ethyl-3-((S)-1-oxo-1-(1-phenyl-1H-1,2,3-triazol-4-yl)methylamino-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: hydrogen bromide; acetic acid / 13 h / 0 - 25 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / diethyl ether / 5 h / 0 - 25 °C / Inert atmosphere

3.1: potassium hydroxide / ethanol / 8.5 h / 0 - 25 °C / Inert atmosphere

3.2: pH Ca_. 4

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere

5.1: copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine / ethanol; water; tert-butyl alcohol / 12 h / 25 °C

With hydrogen bromide; benzotriazol-1-ol; copper(II) sulfate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium hydroxide; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; In diethyl ether; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5.1: |Huisgen Cycloaddition;
DOI:10.1021/jm4006719