N^(α)-benzyloxycarbonyl-N^(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl ester

Base Information

• Chemical Name: N^(α)-benzyloxycarbonyl-N^(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl ester
• CAS No.: 827021-74-9
• Molecular Formula: C₃₃H₃₇N₃O₆S
• Molecular Weight: 603.739

Synonyms:N^(α)-benzyloxycarbonyl-N^(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl ester

Chemical Property of N^(α)-benzyloxycarbonyl-N^(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl ester

Chemical Property:

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Technology Process of N^(α)-benzyloxycarbonyl-N^(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl ester

There total 3 articles about N^(α)-benzyloxycarbonyl-N^(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl 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: 72.0%

5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) + N(α)-benzyloxycarbonyl-L-lysine benzyl ester (5591-94-6) → N(α)-benzyloxycarbonyl-N(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl ester (827021-74-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 6.5h;

DOI:10.1021/ja046164n

Reference yield:

benzyl bromide (100-39-0) → N(α)-benzyloxycarbonyl-N(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl ester (827021-74-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Cs₂CO₃ / methanol / 0 - 20 °C

1.2: 80 percent / dimethylformamide / 48 h / 20 °C

2.1: 90 percent / diethylamine / CH₂Cl₂ / 9 h / 20 °C

3.1: 72 percent / triethylamine / CH₂Cl₂ / 6.5 h / 0 - 20 °C

With caesium carbonate; diethylamine; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja046164n

Reference yield:

N(α)-benzyloxycarbonyl-N(ε)-9-fluorenylmethyloxycarbonyl-L-lysine benzyl ester (827021-73-8) → N(α)-benzyloxycarbonyl-N(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine benzyl ester (827021-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / diethylamine / CH₂Cl₂ / 9 h / 20 °C

2: 72 percent / triethylamine / CH₂Cl₂ / 6.5 h / 0 - 20 °C

With diethylamine; triethylamine; In dichloromethane;

DOI:10.1021/ja046164n

upstream raw materials:

5-(dimethylamino)naphth-1-ylsulfonyl chloride

N^(α)-benzyloxycarbonyl-L-lysine benzyl ester

benzyl bromide

N^(α)-benzyloxycarbonyl-N^(ε)-9-fluorenylmethyloxycarbonyl-L-lysine benzyl ester

Downstream raw materials:

N^(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine

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