methyl N-α,N^ε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate

Base Information

• Chemical Name: methyl N-α,N^ε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate
• CAS No.: 110512-46-4
• Molecular Formula: C₃₇H₅₂N₄O₁₂
• Molecular Weight: 744.839

Synonyms:methyl N-α,N^ε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate

Chemical Property of methyl N-α,N^ε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate

Chemical Property:

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Technology Process of methyl N-α,N^ε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate

There total 4 articles about methyl N-α,N^ε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate 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: 51.0%

methyl 8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate (106174-54-3) + Nα,Nε-bis(benzyloxycarbonyl)-L-lysyl-L-leucine succinimido ester (110512-54-4) → methyl N-α,Nε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate (110512-46-4)

Guidance literature:

With triethylamine; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jm00395a022

Reference yield:

methyl 2,6-anhydro-3-deoxy-D-glycero-D-talo-octonate (106174-63-4) → methyl N-α,Nε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate (110512-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / lithium azide, tetrabromomethane, triphenylphosphine / dimethylformamide / Ambient temperature

2: 90 percent / H₂ / Pd/C / methanol; tetrahydrofuran; ethyl acetate / 2250.2 - 3000.2 Torr

3: 51 percent / Et₃N / methanol / 2 h / Ambient temperature

With lithium azide; carbon tetrabromide; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00395a022

Reference yield:

methyl 2,6-anhydro-8-azido-3,8-dideoxy-D-glycero-D-talo-octonate (106174-79-2) → methyl N-α,Nε-bis(benzyloxycarbonyl)-L-lysyl-L-leucyl>-8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate (110512-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / H₂ / Pd/C / methanol; tetrahydrofuran; ethyl acetate / 2250.2 - 3000.2 Torr

2: 51 percent / Et₃N / methanol / 2 h / Ambient temperature

With hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate;

DOI:10.1021/jm00395a022

upstream raw materials:

methyl 8-amino-2,6-anhydro-3,8-dideoxy-D-glycero-D-talo-octonate

N^α,N^ε-bis(benzyloxycarbonyl)-L-lysyl-L-leucine succinimido ester

methyl 2,6-anhydro-3-deoxy-D-glycero-D-talo-octonate

methyl 2,6-anhydro-8-azido-3,8-dideoxy-D-glycero-D-talo-octonate

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