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

Base Information

• Chemical Name: (2S,3aS,7aS)-1-(N⁶-benzyloxycarbonyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid
• CAS No.: 116586-26-6
• Molecular Formula: C₂₈H₄₀N₄O₈
• Molecular Weight: 560.648

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,3aS,7aS)-1-(N⁶-benzyloxycarbonyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid

There total 1 articles about (2S,3aS,7aS)-1-(N⁶-benzyloxycarbonyl-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: 69.0%

(2S,3aS,7aS)-1-(γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (116586-21-1) + N-benzyloxycarbonyl-L-lysine N-carboxyanhydride (1676-86-4,10289-12-0,47234-64-0,68199-92-8) → (2S,3aS,7aS)-1-(N6-benzyloxycarbonyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (116586-26-6)

Guidance literature:

With potassium hydroxide; potassium carbonate; In 1,4-dioxane; water; at -5 - 0 ℃; for 2h;

DOI:10.1248/cpb.38.110

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:

N-(phenylacetyl)oxysuccinimide (23776-85-4) + (2S,3aS,7aS)-1-(N6-benzyloxycarbonyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (116586-26-6) → (2S,3aS,7aS)-1-(N2-phenylacetyl-L-lysyl-γ-D-glutamyl)octahydro-1H-indole-2-carboxylic acid (128595-10-8)

Guidance literature:

With hydrogen; ammonium formate; sodium hydrogencarbonate; palladium carbon; Multistep reaction; 1) water, THF, 2) methanol;

DOI:10.1248/cpb.38.110

upstream raw materials:

(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-{(R)-4-[6-Amino-2-(4-fluoro-benzoylamino)-hexanoylamino]-4-carboxy-butyryl}-octahydro-indole-2-carboxylic acid

(2S,3aS,7aS)-1-{(R)-4-[6-Amino-2-(4-chloro-benzoylamino)-hexanoylamino]-4-carboxy-butyryl}-octahydro-indole-2-carboxylic acid

(2S,3aS,7aS)-1-{(R)-4-[6-Amino-2-(2-chloro-benzoylamino)-hexanoylamino]-4-carboxy-butyryl}-octahydro-indole-2-carboxylic acid

(2S,3aS,7aS)-1-{(R)-4-[6-Amino-2-(3-phenyl-propionylamino)-hexanoylamino]-4-carboxy-butyryl}-octahydro-indole-2-carboxylic acid

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