N^α-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-N^ε-(benzyloxycarbonyl)lysine methyl ester

Base Information

• Chemical Name: N^α-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-N^ε-(benzyloxycarbonyl)lysine methyl ester
• CAS No.: 111237-91-3
• Molecular Formula: C₄₀H₄₁N₅O₉S
• Molecular Weight: 767.86

Synonyms:N^α-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-N^ε-(benzyloxycarbonyl)lysine methyl ester

Chemical Property of N^α-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-N^ε-(benzyloxycarbonyl)lysine methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N^α-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-N^ε-(benzyloxycarbonyl)lysine methyl ester

There total 3 articles about N^α-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-N^ε-(benzyloxycarbonyl)lysine methyl ester 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: 82.0%

2-nitrobenzenesulfenyl chloride (7669-54-7) + Nα-(benzyloxycarbonyl)tryptophanyl-Nε-(benzyloxycarbonyl)lysine methyl ester (111237-83-3) → Nα-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-Nε-(benzyloxycarbonyl)lysine methyl ester (111237-91-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 0.5h; Ambient temperature;

DOI:10.1021/jm00397a004

Reference yield:

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride (27894-50-4) → Nα-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-Nε-(benzyloxycarbonyl)lysine methyl ester (111237-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Et₃N, DCC / tetrahydrofuran / 2 h / Ambient temperature

2: 82 percent / 1 N HCl / dioxane / 0.5 h / Ambient temperature

With hydrogenchloride; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm00397a004

Reference yield:

N-carbobenzyloxy-L-tryptophane (7432-21-5) → Nα-(benzyloxycarbonyl)-2-<(o-nitrophenyl)sulfenyl>tryptophanyl-Nε-(benzyloxycarbonyl)lysine methyl ester (111237-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Et₃N, DCC / tetrahydrofuran / 2 h / Ambient temperature

2: 82 percent / 1 N HCl / dioxane / 0.5 h / Ambient temperature

With hydrogenchloride; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm00397a004

upstream raw materials:

2-nitrobenzenesulfenyl chloride

N^α-(benzyloxycarbonyl)tryptophanyl-N^ε-(benzyloxycarbonyl)lysine methyl ester

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride

N-carbobenzyloxy-L-tryptophane

Downstream raw materials:

Trp(Nps)-Lys-OMe

cyclo*HCl

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