N^α-benzyloxycarbonyl-N^G-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl ester

Base Information

• Chemical Name: N^α-benzyloxycarbonyl-N^G-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl ester
• CAS No.: 883556-49-8
• Molecular Formula: C₃₇H₅₁N₇O₈S
• Molecular Weight: 753.92

Synonyms:N^α-benzyloxycarbonyl-N^G-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl ester

Chemical Property of N^α-benzyloxycarbonyl-N^G-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl ester

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Technology Process of N^α-benzyloxycarbonyl-N^G-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl ester

There total 3 articles about N^α-benzyloxycarbonyl-N^G-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl 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: 73.0%

Nα-Cbz-NG-Pbf-arginine + tert-butyl (S)-histidinate (759432-08-1) → Nα-benzyloxycarbonyl-NG-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl ester (883556-49-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 - 20 ℃; for 12.33h;

DOI:10.1021/ol060016f

Reference yield:

4-(2-benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethyl)-imidazole-1-carboxylic acid benzyl ester → Nα-benzyloxycarbonyl-NG-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl ester (883556-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / H₂ / Pd/C / methanol / 12 h / 20 °C / 760 Torr

2: 73 percent / EDCI*HCl; HOBt / tetrahydrofuran / 12.33 h / 0 - 20 °C

With hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/ol060016f

Reference yield:

Z-His(imZ)-OH (35016-67-2) → Nα-benzyloxycarbonyl-NG-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginyl-L-histidine tert-butyl ester (883556-49-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / H₂SO₄ / CH₂Cl₂ / -78 - 20 °C

2: 97 percent / H₂ / Pd/C / methanol / 12 h / 20 °C / 760 Torr

3: 73 percent / EDCI*HCl; HOBt / tetrahydrofuran / 12.33 h / 0 - 20 °C

With sulfuric acid; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol060016f

upstream raw materials:

tert-butyl (S)-histidinate

Z-His(imZ)-OH

Downstream raw materials:

C₇₀H₇₈N₁₀O₁₅S

C₆₈H₇₆N₁₀O₁₃S

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