(S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic acid

Base Information

• Chemical Name: (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic acid
• CAS No.: 83816-95-9
• Molecular Formula: C₂₃H₃₀N₄O₁₁
• Molecular Weight: 538.511

Synonyms:(S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic acid

Chemical Property of (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic acid

Chemical Property:

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Technology Process of (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic acid

There total 2 articles about (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic 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:

(S)-2-((S)-4-Benzyloxycarbonyl-4-{(S)-4-benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-butyrylamino)-pentanedioic acid dibenzyl ester (83816-91-5) → (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic acid (83816-95-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; methanol; for 18h; under 760 Torr; Ambient temperature;

DOI:10.1021/jm00356a035

Reference yield:

N-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamic acid α-benzyl ester (79974-14-4) → (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic acid (83816-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / diphenylphosphoryl azide, Et₃N / dimethylformamide / 1.) 0 deg C, 5 h, 2.) RT, 16 h

2: H₂ / 5percent Pd/C / dioxane; methanol / 18 h / 760 Torr / Ambient temperature

With diphenylphosphoranyl azide; hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00356a035

Reference yield: 67.0%

6-bromomethyl-2,4-diaminopteridine hydrobromide (52853-40-4) + (S)-2-{(S)-4-Carboxy-4-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyrylamino}-pentanedioic acid (83816-95-9) → N-methylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamic acid (41600-14-0)

Guidance literature:

In N,N-dimethyl acetamide; at 25 ℃; for 144h;

DOI:10.1021/jm00356a035

upstream raw materials:

(S)-2-((S)-4-Benzyloxycarbonyl-4-{(S)-4-benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-butyrylamino)-pentanedioic acid dibenzyl ester

N-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamic acid α-benzyl ester

Downstream raw materials:

N-methylamino>benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamic acid

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