(2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate

Base Information

• Chemical Name: (2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate
• CAS No.: 1412914-84-1
• Molecular Formula: C₅₂H₆₄N₆O₁₃S
• Molecular Weight: 1013.18
• Mol file: 1412914-84-1.mol

Synonyms:(2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate

Chemical Property of (2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate

There total 13 articles about (2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate 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: 57.0%

(2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-((triisopropylsilyl)oxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate (1412914-83-0) → (2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate (1412914-84-1)

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile; at 0 - 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ja309947n

Reference yield:

6-hydroxy-2,3,5,6,7,7a-hexahydro-1-benzylindole-2-carboxylic acid methyl ester (1412914-77-2) → (2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate (1412914-84-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 5%-palladium/activated carbon; hydrogen / 18 h / 20 °C / Inert atmosphere

2: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 6 h / 0 - 20 °C / Inert atmosphere

3: water; lithium hydroxide / methanol; tetrahydrofuran / 20 h / 20 °C / Inert atmosphere

4: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere

5: sulfur trioxide pyridine complex / pyridine / 3 h / 40 °C / Inert atmosphere

6: pyridine hydrogenfluoride / acetonitrile / 20 h / 0 - 20 °C / Inert atmosphere

With 5%-palladium/activated carbon; water; hydrogen; sulfur trioxide pyridine complex; benzotriazol-1-ol; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja309947n

Reference yield:

(2R,3S)-ethyl 3-(4-(benzyloxy)phenyl)-2,3-dihydroxypropanoate → (2S,3aS,6R,7aS)-1-((2R,3S)-2-((R)-3-(4-(benzyloxy)phenyl)-2-(hydroxy)propanamido)-3-methylpentanoyl)-2-((4-(2,3-dibenzyloxycarbonyl)guanidinobutyl)carbamoyl)octahydro-1H-indol-6-yl hydrogen sulfate (1412914-84-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: trifluoroacetic acid; triethylsilane / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

2.1: dmap; 1H-imidazole / dichloromethane / 24 h / 20 °C / Inert atmosphere

3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

4.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

4.2: 40 h / 20 °C / Inert atmosphere

5.1: water; lithium hydroxide / methanol; tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

6.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 6 h / 0 - 20 °C / Inert atmosphere

7.1: water; lithium hydroxide / methanol; tetrahydrofuran / 20 h / 20 °C / Inert atmosphere

8.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere

9.1: sulfur trioxide pyridine complex / pyridine / 3 h / 40 °C / Inert atmosphere

10.1: pyridine hydrogenfluoride / acetonitrile / 20 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; triethylsilane; dmap; water; sulfur trioxide pyridine complex; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja309947n

upstream raw materials:

6-triisopropylsilyloxy-2,3,5,6,7,7a-hexahydro-1H-indole-2-carboxylic acid methyl ester

6-hydroxy-2,3,5,6,7,7a-hexahydro-1-benzylindole-2-carboxylic acid methyl ester

Methyl (2S,3aS,6R,7aS)-6-hydroxy-octahydroindole-2-carboxylate

ethyl 3-(4-(benzyloxy)phenyl)acrylate

Downstream raw materials:

aeruginosin 98B

Refernces