2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester

Base Information

• Chemical Name: 2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester
• CAS No.: 131618-20-7
• Molecular Formula: C₃₁H₄₂Cl₃N₃O₉Si
• Molecular Weight: 735.134

Synonyms:2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester

Chemical Property of 2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester

There total 3 articles about 2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl 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:

N2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester (124620-52-6) → 2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester (131618-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃COOH / CH₂Cl₂

2: 1.) H₂, 2.) NEt₃, EEDQ / 1.) 10percent Pd/C / 1.) MeOH, AcOH, 2.) CH₂Cl₂

With hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jo00002a005

Reference yield:

O-<(trimethylsilyl)ethyl>diisopropylisourea (131618-25-2) → 2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester (131618-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 4 h / Heating

2: 1.) H₂, 2.) NEt₃, EEDQ / 1.) 10percent Pd/C / 1.) MeOH, AcOH, 2.) CH₂Cl₂

With hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/jo00002a005

Reference yield:

N2-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-serine 1-(trimethylsilyl)ethyl ester (131635-34-2) + C23H25Cl3N2O7 → 2-(benzyloxycarbonyl)-N5-(benzyloxy)-N5-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine 1-(trimethylsilyl)ethyl ester (131618-20-7)

Guidance literature:

With hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; palladium on activated charcoal; Yield given. Multistep reaction; 1.) MeOH, AcOH, 2.) CH₂Cl₂;

DOI:10.1021/jo00002a005

upstream raw materials:

N²-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-serine 1-(trimethylsilyl)ethyl ester

N²-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-<(2,2,2-trichloroethoxy)carbonyl>-L-ornithine 1-tert-butyl ester

O-<(trimethylsilyl)ethyl>diisopropylisourea

Downstream raw materials:

2-(benzyloxycarbonyl)-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-L-serine

foroxymithine

(3S,6S)-3-<3-2-acetyl-N⁵-(benzyloxy)-N⁵-formyl-L-ornithinyl>-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

(3S,6S)-3-<3-2-acetyl-N⁵-(benzyloxy)-N⁵-(2,2,2-trichloroethoxycarbonyl)-L-ornithinyl>-3-acetoxy-L-seryl>-N-(benzyloxy)amino>propyl>-6-<3-propyl>-2,5-piperazinedione

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