{[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1⁽²¹⁾,18⁽²²⁾,19-triene-8-carbonyl]-amino}-acetic acid methyl ester

Base Information

• Chemical Name: {[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1⁽²¹⁾,18⁽²²⁾,19-triene-8-carbonyl]-amino}-acetic acid methyl ester
• CAS No.: 142846-54-6
• Molecular Formula: C₄₂H₅₇N₅O₁₀S₂
• Molecular Weight: 856.074

Synonyms:

Chemical Property of {[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1⁽²¹⁾,18⁽²²⁾,19-triene-8-carbonyl]-amino}-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of {[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1⁽²¹⁾,18⁽²²⁾,19-triene-8-carbonyl]-amino}-acetic acid methyl ester

There total 2 articles about {[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1⁽²¹⁾,18⁽²²⁾,19-triene-8-carbonyl]-amino}-acetic acid methyl 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: 54.0%

1,4-bis(bromomethyl)benzene (623-24-5) + Boc-Lys(Ts)-Lys(Ts)-Gly-OMe (142824-65-5) → {[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1(21),18(22),19-triene-8-carbonyl]-amino}-acetic acid methyl ester (142846-54-6)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79854-6

Reference yield:

Nα-tert-butoxycarbonyl-Nε-tosyl-L-lysine (13734-29-7) → {[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1(21),18(22),19-triene-8-carbonyl]-amino}-acetic acid methyl ester (142846-54-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DIPEA/DCC/HOBt / dimethylformamide

2: 54 percent / Cs₂CO₃ / dimethylformamide

With benzotriazol-1-ol; caesium carbonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79854-6

Reference yield:

{[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1(21),18(22),19-triene-8-carbonyl]-amino}-acetic acid methyl ester (142846-54-6) → {[(8R,11R)-11-tert-Butoxycarbonylamino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1(21),18(22),19-triene-8-carbonyl]-amino}-acetic acid

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79854-6

upstream raw materials:

1,4-bis(bromomethyl)benzene

Boc-Lys(Ts)-Lys(Ts)-Gly-OMe

N^α-tert-butoxycarbonyl-N^ε-tosyl-L-lysine

Downstream raw materials:

{[(8R,11R)-11-Amino-10-oxo-3,16-bis-(toluene-4-sulfonyl)-3,9,16-triaza-bicyclo[16.2.2]docosa-1⁽²¹⁾,18⁽²²⁾,19-triene-8-carbonyl]-amino}-acetic acid pentafluorophenyl ester; compound with trifluoro-acetic acid

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