N₁-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-yl)-N₂-[(4-nitrophenyl)sulfonyl]glycinamide

Base Information

• Chemical Name: N₁-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-yl)-N₂-[(4-nitrophenyl)sulfonyl]glycinamide
• CAS No.: 1297139-33-3
• Molecular Formula: C₂₀H₃₁N₃O₆SSi
• Molecular Weight: 469.634

Synonyms:

Chemical Property of N₁-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-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,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-yl)-N₂-[(4-nitrophenyl)sulfonyl]glycinamide

There total 6 articles about N₁-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-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:

(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,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-yl)-N2-[(4-nitrophenyl)sulfonyl]glycinamide (1297139-33-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: zhan catalyst lB / toluene / 20 °C / Inert atmosphere

2.1: diethylzinc / dichloromethane; hexane / 0.33 h / 0 °C

2.2: 6.33 h / 0 - 20 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

4.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 20 °C

5.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 80 °C

5.2: 1 h / 0 - 20 °C

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

With 2,6-dimethylpyridine; lithium hydroxide monohydrate; diphenyl phosphoryl azide; dihydrogen peroxide; diethylzinc; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; zhan catalyst lB; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

(4R)-3-{[(1S,2S)-2-hydroxy-3-cyclopenten-1-yl]carbonyl}-4-(phenylmethyl)-1,3-oxazolidin-2-one (324741-99-3) → N1-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-yl)-N2-[(4-nitrophenyl)sulfonyl]glycinamide (1297139-33-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diethylzinc / dichloromethane; hexane / 0.33 h / 0 °C

1.2: 6.33 h / 0 - 20 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 20 °C

4.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 80 °C

4.2: 1 h / 0 - 20 °C

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

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

Reference yield:

(4R)-3-{[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]carbonyl}-4-(phenylmethyl)-1,3-oxazolidin-2-one (1297139-25-3) → N1-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-yl)-N2-[(4-nitrophenyl)sulfonyl]glycinamide (1297139-33-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 20 °C

3.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 80 °C

3.2: 1 h / 0 - 20 °C

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

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

upstream raw materials:

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

(4R)-3-{[(1S,2S)-2-hydroxy-3-cyclopenten-1-yl]carbonyl}-4-(phenylmethyl)-1,3-oxazolidin-2-one

(4R)-3-{[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]carbonyl}-4-(phenylmethyl)-1,3-oxazolidin-2-one

(4R)-3-[((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy} bicyclo[3.1.0]hex-3-yl)carbonyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

Downstream raw materials:

4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyI)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}bicyclo[3.1.0]hex-3-yl)-2-piperazinone

4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone

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