[(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-4-yl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-4-yl]-carbamic acid tert-butyl ester
• CAS No.: 136898-43-6
• Molecular Formula: C₃₁H₄₂N₄O₇Se
• Molecular Weight: 661.657

Synonyms:

Chemical Property of [(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-4-yl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-4-yl]-carbamic acid tert-butyl ester

There total 22 articles about [(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-4-yl]-carbamic acid tert-butyl ester 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:

Z-L-leucine hydroxysuccinimide ester (3397-35-1) → [(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl]-carbamic acid tert-butyl ester (136898-43-6,136983-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: KHCO₃ / dioxane / 14 h / 20 °C

2: 100 percent / Bu₄N⁺*F^- / dimethylformamide / 2 h / 20 °C

3: 91 percent / DCC / CH₂Cl₂ / 14 h / -20 - 20 °C

4: 44 percent / 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; 2-methyl-propan-2-ol / 40 h / 90 °C

5: Bu₃P / tetrahydrofuran / 3 h / 20 °C

With tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39910001002

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl]-carbamic acid tert-butyl ester (136898-43-6,136983-39-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / NaHCO₃ / dioxane / 4 h / 20 °C

2: 1.) carbonyldiimidazole (Im₂CO), NaHCO₃ / 1.) THF, 20 deg C, 4 h, 2.) a) 50 deg C, 4 h, b) 20 deg C, 14 h

3: 79 percent / NaNO₂, aq. AcOH / 4 h / 0 °C

4: H₂, AcOH / Pd/C / 16 h / 20 °C

5: KHCO₃ / dioxane / 14 h / 20 °C

6: 100 percent / Bu₄N⁺*F^- / dimethylformamide / 2 h / 20 °C

7: 91 percent / DCC / CH₂Cl₂ / 14 h / -20 - 20 °C

8: 44 percent / 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; 2-methyl-propan-2-ol / 40 h / 90 °C

9: Bu₃P / tetrahydrofuran / 3 h / 20 °C

With tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; acetic acid; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39910001002

Reference yield:

(R)-4-((S)-1-Hydroxy-2-methyl-propyl)-oxazolidin-2-one (136983-35-2) → [(3S,4S,7S)-7-Isobutyl-3-isopropyl-11-(4-nitro-phenylselanyl)-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl]-carbamic acid tert-butyl ester (136898-43-6,136983-39-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 71 percent / pyridine / 72 h / -10 - 20 °C

2: 93 percent / hexamethylphosphoric acid triamide / 5 h / 90 °C

3: 100 percent / 4-dimethylaminopyridine (DMAP), Et₃N / tetrahydrofuran / 4 h / 20 °C

4: 87 percent / Cs₂CO₃ / methanol / 5 h / 20 °C

5: pyridinium dichromate (PDC) / dimethylformamide / 40 h / 20 °C

6: DMAP, cyclohexylcarbodiimide (DCC) / diethyl ether / 20 h / -20 - 20 °C

7: 100 percent / 6 M HCl / dioxane / 5 h / 0 - 20 °C

8: 88 percent / NaHCO₃ / dioxane / 4 h / 20 °C

9: 1.) carbonyldiimidazole (Im₂CO), NaHCO₃ / 1.) THF, 20 deg C, 4 h, 2.) a) 50 deg C, 4 h, b) 20 deg C, 14 h

10: 79 percent / NaNO₂, aq. AcOH / 4 h / 0 °C

11: H₂, AcOH / Pd/C / 16 h / 20 °C

12: KHCO₃ / dioxane / 14 h / 20 °C

13: 100 percent / Bu₄N⁺*F^- / dimethylformamide / 2 h / 20 °C

14: 91 percent / DCC / CH₂Cl₂ / 14 h / -20 - 20 °C

15: 44 percent / 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; 2-methyl-propan-2-ol / 40 h / 90 °C

16: Bu₃P / tetrahydrofuran / 3 h / 20 °C

With pyridine; hydrogenchloride; dmap; dipyridinium dichromate; tributylphosphine; N-cyclohexylcarbodiimide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; potassium hydrogencarbonate; caesium carbonate; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/c39910001002

upstream raw materials:

p-nitrophenyl selenocyanate

((3S,4S,7S)-11-Hydroxy-7-isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-4-yl)-carbamic acid tert-butyl ester

Z-L-leucine hydroxysuccinimide ester

di-tert-butyl dicarbonate

Downstream raw materials:

frangulanine

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