2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide

Base Information

• Chemical Name: 2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide
• CAS No.: 495404-25-6
• Molecular Formula: C₄₂H₅₇N₄O₇P
• Molecular Weight: 760.911

Synonyms:2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide

Chemical Property of 2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide

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Technology Process of 2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide

There total 4 articles about 2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide 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: 63.0%

(3R)-N-{[N-((1S)-1-{N-[(2S)-2-(naphthylmethyl)pent-4-enyl]carbamoyl}-2-carbamoylethyl)carbamoyl]isopropyl}-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)pent-4-enamide (495404-18-7) → 2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide (495404-25-6)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; Heating;

DOI:10.1021/jm0203635

Reference yield:

(2S)-2-amino-N1-[(2S)-2-(naphthylmethyl)-4-pentenyl]butanediamide (401810-36-4) → 2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide (495404-25-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / HOBt; DIPCDI / dimethylformamide / 20 °C

2: piperidine / acetonitrile / 2 h / 20 °C

3: 78 percent / HOBt; DIPCDI / dimethylformamide / 20 °C

4: 63 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

With piperidine; Grubbs catalyst first generation; 1,3-di-tert-butylcarbodiimide; benzotriazol-1-ol; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm0203635

Reference yield:

N-((1S)-1-{N-[(2S)-2-(naphthylmethyl)pent-4-enyl]carbamoyl}-2-carbamoylethyl)-2-amino-2-methylpropanamide (495404-05-2) → 2-[(1S,5S,9R)-3,12,15-triaza-9-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-13,13-dimethyl-5-(naphthylmethyl)-2,11,14-trioxocyclopentadec-7-enyl]acetamide (495404-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / HOBt; DIPCDI / dimethylformamide / 20 °C

2: 63 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

With Grubbs catalyst first generation; 1,3-di-tert-butylcarbodiimide; benzotriazol-1-ol; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0203635

upstream raw materials:

(3R)-N-{[N-((1S)-1-{N-[(2S)-2-(naphthylmethyl)pent-4-enyl]carbamoyl}-2-carbamoylethyl)carbamoyl]isopropyl}-3-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)pent-4-enamide

(2S)-2-amino-N¹-[(2S)-2-(naphthylmethyl)-4-pentenyl]butanediamide

N-((1S)-1-{N-[(2S)-2-(naphthylmethyl)pent-4-enyl]carbamoyl}-2-carbamoylethyl)-2-amino-2-methylpropanamide

{1-[(S)-2-Carbamoyl-1-((S)-2-naphthalen-1-ylmethyl-pent-4-enylcarbamoyl)-ethylcarbamoyl]-1-methyl-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

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