methyl [N^α-(tert-butoxycarbonyl)-N^ε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate

Base Information

• Chemical Name: methyl [N^α-(tert-butoxycarbonyl)-N^ε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate
• CAS No.: 251320-35-1
• Molecular Formula: C₂₉H₄₈ClN₃O₈Si
• Molecular Weight: 630.254

Synonyms:methyl [N^α-(tert-butoxycarbonyl)-N^ε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate

Chemical Property of methyl [N^α-(tert-butoxycarbonyl)-N^ε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate

Chemical Property:

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Technology Process of methyl [N^α-(tert-butoxycarbonyl)-N^ε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate

There total 2 articles about methyl [N^α-(tert-butoxycarbonyl)-N^ε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate 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: 80.0%

tert-butyldimethylsilyl chloride (18162-48-6) + methyl [Nα-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate (251320-34-0) → methyl [Nα-(tert-butoxycarbonyl)-Nε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate (251320-35-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 0.5h;

DOI:10.1016/S0040-4020(99)00689-4

Reference yield:

Boc-(S)-Lys(2-Cl-Z)-OH (54613-99-9) → methyl [Nα-(tert-butoxycarbonyl)-Nε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate (251320-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / BOP; DIEA / CH₂Cl₂ / 1 h / 20 °C

2: 80 percent / imidazole / dimethylformamide / 0.5 h

With 1H-imidazole; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: silylation;

DOI:10.1016/S0040-4020(99)00689-4

Reference yield:

methyl [Nα-(tert-butoxycarbonyl)-Nε-(2-chlorobenzyloxycarbonyl)-L-lysyl]-O-(tert-butyl-dimethylsilyl)-L-serinate (251320-35-1) → 2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanethioylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

Guidance literature:

With Lawessons reagent; In 1,4-dioxane; at 70 ℃; for 0.666667h;

DOI:10.1016/S0040-4020(99)00689-4

upstream raw materials:

tert-butyldimethylsilyl chloride

methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate

Boc-(S)-Lys(2-Cl-Z)-OH

Downstream raw materials:

(1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylic acid

methyl (1'S,4S)-2-[1-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylate

methyl (1'S,4S)-2-[1'-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-2-thiazoline-4-carboxylate

methyl (2S)-N-[2-(tert-butoxycarbonylamino)-6-(2-chlorobenzyloxycarbonylamino)-hexanethiocarboxyl]-L-serinate

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