(3'S,4S,9'S,11'S)-2,2',5,8'-tetraoxo-1-phenyl-11'-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.0^3,7]dodecane]-11'-carboxylic acid

Base Information

• Chemical Name: (3'S,4S,9'S,11'S)-2,2',5,8'-tetraoxo-1-phenyl-11'-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.0^3,7]dodecane]-11'-carboxylic acid
• CAS No.: 1407162-82-6
• Molecular Formula: C₃₇H₃₆N₆O₉
• Molecular Weight: 708.728

Synonyms:

Chemical Property of (3'S,4S,9'S,11'S)-2,2',5,8'-tetraoxo-1-phenyl-11'-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.0^3,7]dodecane]-11'-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (3'S,4S,9'S,11'S)-2,2',5,8'-tetraoxo-1-phenyl-11'-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.0^3,7]dodecane]-11'-carboxylic acid

There total 12 articles about (3'S,4S,9'S,11'S)-2,2',5,8'-tetraoxo-1-phenyl-11'-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.0^3,7]dodecane]-11'-carboxylic acid 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-formylbenzyl allyl chloroformate (1407162-52-0) + (3'S,4S,9'S,11'S)-11'-amino-2,2',5,8'-tetraoxo-1-phenyl-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.03,7]dodecane]-11'-carboxylic acid (1407162-81-5) → (3'S,4S,9'S,11'S)-2,2',5,8'-tetraoxo-1-phenyl-11'-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.03,7]dodecane]-11'-carboxylic acid (1407162-82-6)

Guidance literature:

2-formylbenzyl allyl chloroformate; (3'S,4S,9'S,11'S)-11'-amino-2,2',5,8'-tetraoxo-1-phenyl-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.0^3,7]dodecane]-11'-carboxylic acid; In methanol; at 20 ℃; for 0.5h;

With sodium cyanoborohydride; In methanol; at 20 ℃; for 12h;

DOI:10.1021/ja3069648

Reference yield:

C19H23N3O6 → (3'S,4S,9'S,11'S)-2,2',5,8'-tetraoxo-1-phenyl-11'-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.03,7]dodecane]-11'-carboxylic acid (1407162-82-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogen; palladium on activated charcoal / tetrahydrofuran / 20 °C

2.1: di-tert-butyl dicarbonate; dmap / tetrahydrofuran / 1.5 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine; dmap / tetrahydrofuran / 24 h / 20 °C

4.1: chlorotriisopropylsilane; trifluoroacetic acid / 4 h / 20 °C

5.1: triethylamine / tetrahydrofuran / 0 - 20 °C

6.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

6.2: 24 h / 20 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane / dichloromethane; N,N-dimethyl-formamide / 24 h / 20 °C

8.1: methanol / 0.5 h / 20 °C

8.2: 12 h / 20 °C

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chlorotriisopropylsilane; di-tert-butyl dicarbonate; palladium on activated charcoal; phenylsilane; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja3069648

Reference yield:

(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-aminopyrrolidine-3-carboxylic acid (526222-99-1) → (3'S,4S,9'S,11'S)-2,2',5,8'-tetraoxo-1-phenyl-11'-({[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}amino)-3-(pyridin-4-ylmethyl)-1',7'-diazaspiro[imidazolidine-4,5'-tricyclo[7.3.0.03,7]dodecane]-11'-carboxylic acid (1407162-82-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: methanol / 0.5 h / 20 °C

1.2: 12 h / 20 °C

2.1: triethylamine / tetrahydrofuran / 24 h / 20 °C

3.1: hydrogen bromide / dichloromethane; acetic acid / 1.5 h / 20 °C

4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

4.2: 24 h / 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane / dichloromethane; N,N-dimethyl-formamide / 24 h / 20 °C

6.1: methanol / 0.5 h / 20 °C

6.2: 12 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane; hydrogen bromide; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ja3069648

upstream raw materials:

7,8-di-tert-butyl (5S,8S)-2,4-dioxo-1,3,7-triazaspiro[4,4]nonane-7,8-dicarboxylate

pyridine-4-carbaldehyde

(3S,5S)-3-amino-1,5-bis(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

(3S,5S)-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)-3-aminopyrrolidine-3-carboxylic acid

Downstream raw materials:

(3'S,4S,5''S,5'''S,9'S,11'S)-4''-[(2,4-dimethoxyphenyl)methyl]-2,2',3'',5,6'',8'-hexaoxo-1-phenyl-1''-{[2-({[(prop-2-en-1-yloxy)carbonyl]oxy}methyl)phenyl]methyl}-3-(pyridin-4-ylmethyl)trispiro[imidazoline-4,5'-[1,7]diazatricyclo[7.3.0.0^3,7]dodecane-11',2''-piperazine-5'',3'''-pyrrolidine]-5'''-carboxylic acid

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