N₁-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl] oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-N₂-[(4-nitrophenyl)sulfonyl]glycinamide

Base Information

• Chemical Name: N₁-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl] oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-N₂-[(4-nitrophenyl)sulfonyl]glycinamide
• CAS No.: 1431285-91-4
• Molecular Formula: C₂₇H₃₇N₃O₆SSi
• Molecular Weight: 559.759

Synonyms:

Chemical Property of N₁-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl] oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-N₂-[(4-nitrophenyl)sulfonyl]glycinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N₁-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl] oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-N₂-[(4-nitrophenyl)sulfonyl]glycinamide

There total 5 articles about N₁-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl] oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-N₂-[(4-nitrophenyl)sulfonyl]glycinamide 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:

2-[(4-nitrobenzene)sulfonamido]acetic acid (15054-44-1) + (1E,3S,4S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-phenyl-1,6-heptadien-4-amine (1431285-90-3) → N1-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl] oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-N2-[(4-nitrophenyl)sulfonyl]glycinamide (1431285-91-4)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1021/jm400125h

Reference yield:

(4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one (1297139-24-2) → N1-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl] oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-N2-[(4-nitrophenyl)sulfonyl]glycinamide (1431285-91-4)

Guidance literature:

Multi-step reaction with 5 steps

1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 20 °C

2: triethylamine; diphenylphosphoranyl azide / toluene / 80 °C

3: potassium hydroxide / ethanol / Inert atmosphere; Reflux

4: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

5: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 5 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide monohydrate; diphenylphosphoranyl azide; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm400125h

Reference yield:

(4S,5S)-5-[(E)-2-phenylethenyl]-4-(2-propen-1-yl)-1,3-oxazolidin-2-one (1431285-88-9) → N1-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl] oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-N2-[(4-nitrophenyl)sulfonyl]glycinamide (1431285-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / ethanol / Inert atmosphere; Reflux

2: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 5 h / 20 °C

With 2,6-dimethylpyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm400125h

upstream raw materials:

2-[(4-nitrobenzene)sulfonamido]acetic acid

(1E,3S,4S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-phenyl-1,6-heptadien-4-amine

(4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid

Downstream raw materials:

1-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-4-[(4-nitrophenyl)sulfonyl]-2-piperazinone

1-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-2-piperazinone

4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3E)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-4-phenyl-1-(2-propen-1-yl)-3-buten-1-yl]-2-piperazinone

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