tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-carboxylate
• CAS No.: 1346171-55-8
• Molecular Formula: C₃₆H₄₉N₅O₄Si
• Molecular Weight: 643.902

Synonyms:tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-carboxylate

There total 15 articles about tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-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:

tert-butyl (2S,5R)-2-(3-amino-4-{[(2S)-2-(2-oxopyrimidin-1(2H)-yl)propanoyl]amino}benzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate (1346171-54-7) → tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-carboxylate (1346171-55-8)

Guidance literature:

With acetic acid; at 100 ℃; for 1h; Inert atmosphere;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-carboxylate (1346171-55-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4.17 h / 20 °C / Inert atmosphere

2.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 20 °C / Inert atmosphere

2.2: 16 h / 105 °C / Inert atmosphere

3.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

4.1: pyrrolidine / N,N-dimethyl-formamide / 3 h / 80 °C

4.2: 3 h / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C

5.2: 0 - 20 °C

6.1: triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr

8.1: acetic acid; 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one / 2 h / 0 °C / Inert atmosphere

9.1: zinc; acetic acid / 1 h / Inert atmosphere

10.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / Inert atmosphere

11.1: acetic acid / 1 h / 100 °C / Inert atmosphere

With pyrrolidine; hydrogenchloride; copper(l) iodide; 1-hydroxy-7-aza-benzotriazole; diphenyl phosphoryl azide; 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; zinc; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

(4S)-3-{(2R)-2-[(S)-hydroxy(phenyl)methyl]hex-5-ynoyl}-4-phenyl-1,3-oxazolidin-2-one (1190391-61-7) → tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-({2-[(1S)-1-(2-oxopyrimidin-1(2H)-yl)ethyl]-1H-benzimidazol-6-yl}methyl)pyrrolidine-1-carboxylate (1346171-55-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 3 h / 0 - 5 °C / Inert atmosphere

1.2: 0 - 5 °C

1.3: 0 °C / pH 3

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4.17 h / 20 °C / Inert atmosphere

3.1: triethylamine; diphenyl phosphoryl azide / toluene / 5 h / 20 °C / Inert atmosphere

3.2: 16 h / 105 °C / Inert atmosphere

4.1: triethylamine; copper(l) iodide / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

5.1: pyrrolidine / N,N-dimethyl-formamide / 3 h / 80 °C

5.2: 3 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C

6.2: 0 - 20 °C

7.1: triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 2585.81 Torr

9.1: acetic acid; 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one / 2 h / 0 °C / Inert atmosphere

10.1: zinc; acetic acid / 1 h / Inert atmosphere

11.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / Inert atmosphere

12.1: acetic acid / 1 h / 100 °C / Inert atmosphere

With pyrrolidine; hydrogenchloride; copper(l) iodide; 1-hydroxy-7-aza-benzotriazole; diphenyl phosphoryl azide; 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one; hydrogen; dihydrogen peroxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hydroxide; zinc; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

tert-butyldimethylsilyl chloride

di-tert-butyl dicarbonate

tert-butyl (2S,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate

4-({(5R)-5-[(R)-([tert-butyl(dimethyl)silyl]oxy)(phenyl)methyl]pyrrolidin-2-yl}methyl)aniline

Downstream raw materials:

1-{(1S)-1-[6-({(2S,5R)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl}methyl)-1H-benzimidazol-2-yl]ethyl}pyrimidin-2(1H)-one

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