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

Base Information

• Chemical Name: benzyl [(6S,9S,12S)-6-(hydroxymethyl)-9-(2-methylpropyl)-8,11-dioxo-1,7,10,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-dien-12-yl]carbamate
• CAS No.: 1416327-07-5
• Molecular Formula: C₂₆H₃₇N₅O₅
• Molecular Weight: 499.61

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 6 articles about benzyl [(6S,9S,12S)-6-(hydroxymethyl)-9-(2-methylpropyl)-8,11-dioxo-1,7,10,15-tetraazabicyclo[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: 98.0%

methyl (6S,9S,12S)-12-{[(benzyloxy)carbonyl]amino}-9-(2-methylpropyl)-8,11-dioxo-1,7,10,15-tetraazabicyclo[12.2.1]heptadeca-14(17),15-diene-6-carboxylate (1416327-06-4) → benzyl [(6S,9S,12S)-6-(hydroxymethyl)-9-(2-methylpropyl)-8,11-dioxo-1,7,10,15-tetraazabicyclo[12.2.1]heptadeca-14(17),15-dien-12-yl]carbamate (1416327-07-5)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1002/cbdv.201200320

Reference yield:

tert-butyl N-[ (benzyloxy)carbonyl]-1-((5S)-5-{[(tert-butoxy)carbonyl]amino}-6-methoxy-6-oxohexyl)-L-histidyl-L-leucinate (1416327-13-3) → benzyl [(6S,9S,12S)-6-(hydroxymethyl)-9-(2-methylpropyl)-8,11-dioxo-1,7,10,15-tetraazabicyclo[12.2.1]heptadeca-14(17),15-dien-12-yl]carbamate (1416327-07-5)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 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 / Inert atmosphere

3: lithium borohydride / tetrahydrofuran / 20 °C / Inert atmosphere

With lithium borohydride; 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; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/cbdv.201200320

Reference yield:

tert-butyl N-[(benzyloxy)carbonyl]-L-histidyl-L-leucinate (1416327-12-2) → benzyl [(6S,9S,12S)-6-(hydroxymethyl)-9-(2-methylpropyl)-8,11-dioxo-1,7,10,15-tetraazabicyclo[12.2.1]heptadeca-14(17),15-dien-12-yl]carbamate (1416327-07-5)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: 4 h / -15 - -5 °C / Inert atmosphere

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 / Inert atmosphere

4.1: lithium borohydride / tetrahydrofuran / 20 °C / Inert atmosphere

With lithium borohydride; sodium hydride; 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; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/cbdv.201200320

upstream raw materials:

tert-butyl N-[(benzyloxy)carbonyl]-L-histidyl-L-leucinate

N-[(benzyloxy)carbonyl]-L-histidine

L-leucine tert-butyl ester

methyl (6S,9S,12S)-12-{[(benzyloxy)carbonyl]amino}-9-(2-methylpropyl)-8,11-dioxo-1,7,10,15-tetraazabicyclo[12.2.1]heptadeca-14⁽¹⁷⁾,15-diene-6-carboxylate

Downstream raw materials:

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

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