methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16⁽¹⁹⁾,17-diene-12-carboxylate

Base Information

• Chemical Name: methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16⁽¹⁹⁾,17-diene-12-carboxylate
• CAS No.: 1417159-48-8
• Molecular Formula: C₂₇H₃₈N₆O₇
• Molecular Weight: 558.635

Synonyms:methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16⁽¹⁹⁾,17-diene-12-carboxylate

Chemical Property of methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16⁽¹⁹⁾,17-diene-12-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16⁽¹⁹⁾,17-diene-12-carboxylate

There total 4 articles about methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16⁽¹⁹⁾,17-diene-12-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: 80.0%

methyl (5S,8S,11S)-5-(4-azidobutyl)-8-isobutyl-3,6,9-trioxo-1-phenyl-11-((prop-2-yn-1-yloxy)methyl)-2-oxa-4,7,10-triazadodecan-12-oate (1417159-44-4) → methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16(19),17-diene-12-carboxylate (1417159-48-8)

Guidance literature:

methyl (5S,8S,11S)-5-(4-azidobutyl)-8-isobutyl-3,6,9-trioxo-1-phenyl-11-((prop-2-yn-1-yloxy)methyl)-2-oxa-4,7,10-triazadodecan-12-oate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

With copper(I) bromide; In dichloromethane; for 7h; Inert atmosphere;

DOI:10.1039/c2ob26637g

Reference yield:

(S)-2-((S)-6-azido-2-(((benzyloxy)carbonyl)amino)hexanamido)-4-methylpentanoic acid (1359969-70-2) → methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16(19),17-diene-12-carboxylate (1417159-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2.2: 7 h / Inert atmosphere

With benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1039/c2ob26637g

Reference yield:

C7H11NO3*(x)ClH → methyl (6S,9S,12S)-6-(((benzyloxy)carbonyl)amino)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16(19),17-diene-12-carboxylate (1417159-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2.2: 7 h / Inert atmosphere

With benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1039/c2ob26637g

upstream raw materials:

(S)-2-((S)-6-azido-2-(((benzyloxy)carbonyl)amino)hexanamido)-4-methylpentanoic acid

methyl (5S,8S,11S)-5-(4-azidobutyl)-8-isobutyl-3,6,9-trioxo-1-phenyl-11-((prop-2-yn-1-yloxy)methyl)-2-oxa-4,7,10-triazadodecan-12-oate

(S)-2-[(tert-butoxycarbonyl)amino]-3-(prop-2-yn-1-yloxy)propanoic acid

Downstream raw materials:

benzyl ((6S,9S,12R)-12-(hydroxymethyl)-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16⁽¹⁹⁾,17-dien-6-yl)carbamate

benzyl ((6S,9S,12S)-12-formyl-9-isobutyl-7,10-dioxo-14-oxa-1,8,11,17,18-pentaazabicyclo[14.2.1]nonadeca-16⁽¹⁹⁾,17-dien-6-yl)carbamate

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