(2S,3aS,7aS)-1-(N⁶-Z-N²-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid

Base Information

• Chemical Name: (2S,3aS,7aS)-1-(N⁶-Z-N²-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid
• CAS No.: 116586-27-7
• Molecular Formula: C₃₄H₄₃N₅O₉
• Molecular Weight: 665.744

Synonyms:(2S,3aS,7aS)-1-(N⁶-Z-N²-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid

Chemical Property of (2S,3aS,7aS)-1-(N⁶-Z-N²-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3aS,7aS)-1-(N⁶-Z-N²-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid

There total 3 articles about (2S,3aS,7aS)-1-(N⁶-Z-N²-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid 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: 85.0%

nicotinic acid succinimidyl ester (78348-28-4) + (2S,3aS,7aS)-1-(N6-benzyloxycarbonyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (116586-26-6) → (2S,3aS,7aS)-1-(N6-Z-N2-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (116586-27-7)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; Ambient temperature;

DOI:10.1248/cpb.38.110

Reference yield:

(2S,3aS,7aS)-1-(γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (116586-21-1) → (2S,3aS,7aS)-1-(N6-Z-N2-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (116586-27-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / potassium hydroxide, potassium carbonate / dioxane; H₂O / 2 h / -5 - 0 °C

2: 85 percent / NaHCO₃ / tetrahydrofuran; H₂O / Ambient temperature

With potassium hydroxide; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1248/cpb.38.110

Reference yield:

N-benzyloxycarbonyl-L-lysine N-carboxyanhydride (1676-86-4,10289-12-0,47234-64-0,68199-92-8) → (2S,3aS,7aS)-1-(N6-Z-N2-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (116586-27-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / potassium hydroxide, potassium carbonate / dioxane; H₂O / 2 h / -5 - 0 °C

2: 85 percent / NaHCO₃ / tetrahydrofuran; H₂O / Ambient temperature

With potassium hydroxide; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1248/cpb.38.110

upstream raw materials:

nicotinic acid succinimidyl ester

(2S,3aS,7aS)-1-(N⁶-benzyloxycarbonyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid

(2S,3aS,7aS)-1-(γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid

N-benzyloxycarbonyl-L-lysine N-carboxyanhydride

Downstream raw materials:

(2S,3aS,7aS)-1-(N²-nicotinoyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid

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