benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-1¹H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate

Base Information

• Chemical Name: benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-1¹H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate
• CAS No.: 1443654-66-7
• Molecular Formula: C₂₇H₃₉N₇O₆
• Molecular Weight: 557.65

Synonyms:benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-1¹H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate

Chemical Property of benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-1¹H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-1¹H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate

There total 7 articles about benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-1¹H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-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: 84.0%

methyl (3S,6S,9S,Z)-3-(((benzyloxy)carbonyl)amino)-6-isobutyl-4,7,12-trioxo-11H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-9-carboxylate (1443654-65-6) → benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-11H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate (1443654-66-7)

Guidance literature:

With lithium borohydride; ethanol; In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield:

1-((1-methoxy-4-methyl-1-oxopentan-2-yl)amino)-1-oxopent-4-yn-2-aminium chloride (1443654-61-2) → benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-11H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate (1443654-66-7)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane

2: lithium hydroxide; water / tetrahydrofuran

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

4: copper(I) bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane

5: lithium borohydride / tetrahydrofuran

With lithium borohydride; water; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; copper(I) bromide; lithium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.05.021

Reference yield:

methyl (S)-2-((S)-2-(((benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoate (1417159-39-7) → benzyl ((3S,6S,9S,Z)-9-(hydroxymethyl)-6-isobutyl-4,7,12-trioxo-11H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate (1443654-66-7)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium hydroxide; water / tetrahydrofuran

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide

3: copper(I) bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane

4: lithium borohydride / tetrahydrofuran

With lithium borohydride; water; 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; copper(I) bromide; lithium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.05.021

upstream raw materials:

methyl (3S,6S,9S,Z)-3-(((benzyloxy)carbonyl)amino)-6-isobutyl-4,7,12-trioxo-1¹H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-9-carboxylate

(S)-Leu-OMe

1-((1-methoxy-4-methyl-1-oxopentan-2-yl)amino)-1-oxopent-4-yn-2-aminium chloride

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

Downstream raw materials:

benzyl ((3S,6S,9S,Z)-9-formyl-6-isobutyl-4,7,12-trioxo-1¹H-5,8,13-triaza-1(4,1)-triazolacyclohexadecaphane-3-yl)carbamate

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