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

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Chemical Name:methyl (2S)-N-[2-(tert-butoxycarbonylamino)-6-(2-chlorobenzyloxycarbonylamino)-hexanethiocarboxyl]-L-serinate
CAS No.:251320-36-2
Molecular Formula:C₂₃H₃₄ClN₃O₇S
Molecular Weight:532.058
Hs Code.:

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

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

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

There total 4 articles about methyl (2S)-N-[2-(tert-butoxycarbonylamino)-6-(2-chlorobenzyloxycarbonylamino)-hexanethiocarboxyl]-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: 85.0%

: 2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanethioylamino]-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

: 251320-36-2
methyl (2S)-N-[2-(tert-butoxycarbonylamino)-6-(2-chlorobenzyloxycarbonylamino)-hexanethiocarboxyl]-L-serinate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.416667h;
DOI:10.1016/S0040-4020(99)00689-4

Reference yield:

: 54613-99-9
Boc-(S)-Lys(2-Cl-Z)-OH

: 251320-36-2
methyl (2S)-N-[2-(tert-butoxycarbonylamino)-6-(2-chlorobenzyloxycarbonylamino)-hexanethiocarboxyl]-L-serinate

Guidance literature:: Multi-step reaction with 4 steps

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

2: 80 percent / imidazole / dimethylformamide / 0.5 h

3: 3.70 g / Lawesson reagent / dioxane / 0.67 h / 70 °C

4: 85 percent / 1N Bu₄NF / tetrahydrofuran / 0.42 h

With Lawessons reagent; 1H-imidazole; tetrabutyl ammonium fluoride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: silylation / 3: sulfurization / 4: Hydrolysis;
DOI:10.1016/S0040-4020(99)00689-4

Reference yield:

: 251320-34-0
methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate

: 251320-36-2
methyl (2S)-N-[2-(tert-butoxycarbonylamino)-6-(2-chlorobenzyloxycarbonylamino)-hexanethiocarboxyl]-L-serinate

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / imidazole / dimethylformamide / 0.5 h

2: 3.70 g / Lawesson reagent / dioxane / 0.67 h / 70 °C

3: 85 percent / 1N Bu₄NF / tetrahydrofuran / 0.42 h

With Lawessons reagent; 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; 1: silylation / 2: sulfurization / 3: Hydrolysis;
DOI:10.1016/S0040-4020(99)00689-4