methyl N⁶-[(benzyloxy)carbonyl]-N²-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate

Base Information

• Chemical Name: methyl N⁶-[(benzyloxy)carbonyl]-N²-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate
• CAS No.: 98385-71-8
• Molecular Formula: C₃₁H₄₀N₄O₇
• Molecular Weight: 580.681

Synonyms:methyl N⁶-[(benzyloxy)carbonyl]-N²-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate

Chemical Property of methyl N⁶-[(benzyloxy)carbonyl]-N²-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate

Chemical Property:

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Technology Process of methyl N⁶-[(benzyloxy)carbonyl]-N²-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate

There total 4 articles about methyl N⁶-[(benzyloxy)carbonyl]-N²-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate 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: 95.0%

Boc-Lys(Z)-OSu (34404-36-9) + L-tryptophan methyl ester (4299-70-1) → methyl N6-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate (98385-71-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/ol048845t

Reference yield: 61.0%

Boc-Lys(Z)-OH (2389-45-9) + (S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → methyl N6-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate (98385-71-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/acs.orglett.0c00033

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → methyl N6-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-lysyl-L-tryptophanate (98385-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 20 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 0 - 20 °C

With thionyl chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1021/acs.orglett.0c00033

upstream raw materials:

Boc-Lys(Z)-OSu

L-tryptophan methyl ester

L-Tryptophan

Boc-Lys(Z)-OH

Downstream raw materials:

(S)-2-((S)-2-Amino-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester

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