(8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid benzyl ester

Base Information

• Chemical Name: (8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid benzyl ester
• CAS No.: 132235-84-8
• Molecular Formula: C₂₉H₃₁N₅O₅
• Molecular Weight: 529.596

Synonyms:(8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid benzyl ester

Chemical Property of (8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid benzyl ester

There total 4 articles about (8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid benzyl 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: 78.0%

L-prolyl-L-phenylalanyl-Nim-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate (132259-60-0) → (8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.04,8]nonadeca-16(19),17-diene-14-carboxylic acid benzyl ester (132235-84-8)

Guidance literature:

With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; for 120h;

DOI:10.1021/jm00108a006

Reference yield:

Nα-(tert-butyloxycarbonyl)-Nim-tosyl-L-histidine benzyl ester (132259-57-5) → (8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.04,8]nonadeca-16(19),17-diene-14-carboxylic acid benzyl ester (132235-84-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.9 g / trifluoroacetic acid / CH₂Cl₂ / 1 h

2: diisopropylethylamine, diethylphosphoryl cyanide / CH₂Cl₂ / 18 h

3: 100 percent / 1-hydroxybenzotriazole / methanol / 18 h

4: 72 percent / diisopropylethylamine / CH₂Cl₂ / 18 h

5: 100 percent / diisopropylethylamine / CH₂Cl₂ / 1.25 h

6: 78 percent / 4-(dimethylamino)pyridine, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 120 h

With dmap; diethylphosphoryl cyanide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1021/jm00108a006

Reference yield:

Nα-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-Nim-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester (132259-58-6) → (8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.04,8]nonadeca-16(19),17-diene-14-carboxylic acid benzyl ester (132235-84-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / diisopropylethylamine / CH₂Cl₂ / 1.25 h

2: 78 percent / 4-(dimethylamino)pyridine, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 120 h

With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jm00108a006

upstream raw materials:

L-prolyl-L-phenylalanyl-N^im-(carboxymethyl)-L-histidine benzyl ester trifluoroacetate

N^α-(tert-butyloxycarbonyl)-N^im-tosyl-L-histidine benzyl ester

N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-<(tert-butyloxycarbonyl)methyl>-L-histidine benzyl ester

N^α-(tert-butyloxycarbonyl)-L-prolyl-L-phenylalanyl-N^im-tosyl-L-histidine benzyl ester

Downstream raw materials:

(8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid

(8S,11S,14S)-11-Benzyl-3,9,12-trioxo-1,4,10,13,17-pentaaza-tricyclo[14.2.1.0^4,8]nonadeca-16⁽¹⁹⁾,17-diene-14-carboxylic acid [(1S,2S,4S)-1-cyclohexylmethyl-2-hydroxy-5-methyl-4-((S)-2-methyl-butylcarbamoyl)-hexyl]-amide

C₄₉H₆₉N₉O₇

C₅₅H₈₃N₉O₇Si

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