benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-12-yl)carbamate

Base Information

• Chemical Name: benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-12-yl)carbamate
• CAS No.: 1417159-38-6
• Molecular Formula: C₂₅H₃₄N₆O₅
• Molecular Weight: 498.582

Synonyms:benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-12-yl)carbamate

Chemical Property of benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-12-yl)carbamate

Chemical Property:

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Technology Process of benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-12-yl)carbamate

There total 11 articles about benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-12-yl)carbamate 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%

benzyl ((6S,9S,12S)-6-(hydroxymethyl)-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14(17),15-dien-12-yl)carbamate (1417159-37-5) → benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14(17),15-dien-12-yl)carbamate (1417159-38-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.25h; Inert atmosphere;

DOI:10.1039/c2ob26637g

Reference yield:

Cbz-L-propargylglycine-OH (869116-13-2) → benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14(17),15-dien-12-yl)carbamate (1417159-38-6)

Guidance literature:

Multi-step reaction with 6 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: lithium hydroxide / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

2.2: pH 7 / Inert atmosphere

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

4.2: 7 h / Inert atmosphere

5.1: lithium borohydride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere; Cooling with ice

6.1: Dess-Martin periodane / dichloromethane / 1.25 h / 20 °C / Inert atmosphere

With lithium borohydride; benzotriazol-1-ol; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c2ob26637g

Reference yield:

methyl (6S,9S,12S)-12-(((benzyloxy)carbonyl)amino)-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14(17),15-diene-6-carboxylate (1417159-36-4) → benzyl ((6S,9S,12S)-6-formyl-9-isobutyl-8,11-dioxo-1,7,10,15,16-pentaazabicyclo[12.2.1]heptadeca-14(17),15-dien-12-yl)carbamate (1417159-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium borohydride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere; Cooling with ice

2: Dess-Martin periodane / dichloromethane / 1.25 h / 20 °C / Inert atmosphere

With lithium borohydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c2ob26637g

upstream raw materials:

Cbz-L-propargylglycine-OH

methyl (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoate

(S)-2-((S)-2-(((benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoic acid

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

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