benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-6-yl]carbamate

Base Information

• Chemical Name: benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-6-yl]carbamate
• CAS No.: 1416327-11-1
• Molecular Formula: C₂₆H₃₅N₅O₅
• Molecular Weight: 497.594

Synonyms:benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-6-yl]carbamate

Chemical Property of benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-6-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-6-yl]carbamate

There total 10 articles about benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-6-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: 40.0%

benzyl [(6S,9S,12S)-12-(hydroxymethyl)-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14(17),15-dien-6-yl]carbamate (1416327-10-0) → benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14(17),15-dien-6-yl]carbamate (1416327-11-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/cbdv.201200320

Reference yield:

methyl N-[(tert-butoxy)carbonyl]-L-leucyl-L-histidinate → benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14(17),15-dien-6-yl]carbamate (1416327-11-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; hexane / 0.5 h / -15 °C

1.2: 4 h / -15 - -5 °C

2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

4.1: lithium borohydride / tetrahydrofuran; methanol / 20 °C

5.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

With lithium borohydride; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/cbdv.201200320

Reference yield:

L-Histidine methyl ester (1499-46-3) → benzyl [(6S,9S,12S)-12-formyl-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14(17),15-dien-6-yl]carbamate (1416327-11-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; hexane / 0.5 h / -15 °C

2.2: 4 h / -15 - -5 °C

3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

5.1: lithium borohydride / tetrahydrofuran; methanol / 20 °C

6.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

With lithium borohydride; 1-hydroxy-7-aza-benzotriazole; sodium hydride; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/cbdv.201200320

upstream raw materials:

benzyl [(6S,9S,12S)-12-(hydroxymethyl)-9-(2-methylpropyl)-7,10-dioxo-1,8,11,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-6-yl]carbamate

C₂₇H₃₉N₅O₇

N-tert-butoxycarbonyl-L-leucine

L-Histidine methyl ester

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