N^α,N^α'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-N^ε-(benzoyloxy)-L-lysine methyl ester>

Base Information

• Chemical Name: N^α,N^α'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-N^ε-(benzoyloxy)-L-lysine methyl ester>
• CAS No.: 145385-50-8
• Molecular Formula: C₅₆H₆₄N₄O₁₅
• Molecular Weight: 1033.14

Synonyms:N^α,N^α'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-N^ε-(benzoyloxy)-L-lysine methyl ester>

Chemical Property of N^α,N^α'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-N^ε-(benzoyloxy)-L-lysine methyl ester>

Chemical Property:

Purity/Quality:

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Technology Process of N^α,N^α'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-N^ε-(benzoyloxy)-L-lysine methyl ester>

There total 4 articles about N^α,N^α'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-N^ε-(benzoyloxy)-L-lysine 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: 28.0%

3-(tert-butoxycarbonyl)-3-hydroxypentanedioic acid (114340-52-2) + Nε-(benzoyloxy)-Nε-cinnamoyl-L-lysine methyl ester trifluoroacetic acid salt → Nα,Nα'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-Nε-(benzoyloxy)-L-lysine methyl ester> (145385-50-8)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; 1) DMF, 0 deg C, 10 min, 2) DMF, a) 0 deg C, 3 h, b) to r.t., overnight;

DOI:10.1021/jo00052a030

Reference yield:

N-α-(tert-butoxycarbonyl)-L-lysine methyl ester (55757-60-3) → Nα,Nα'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-Nε-(benzoyloxy)-L-lysine methyl ester> (145385-50-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Na₂CO₃, 2) trans-cinnamoyl chloride / 1) CH₂Cl₂, r.t., 3 h, 2) H₂O, CH₂Cl₂, overnight

2: 100 percent / 0.5 h / 0 °C

3: 28 percent / 1) diphenyl phosphorazidate, 2) Et₃N / 1) DMF, 0 deg C, 10 min, 2) DMF, a) 0 deg C, 3 h, b) to r.t., overnight

With diphenyl phosphoryl azide; sodium carbonate; triethylamine; Cinnamoyl chloride;

DOI:10.1021/jo00052a030

Reference yield:

Nε-cinnamoyl-Nε-(benzoyloxy)-Nα-BOC-L-lysine methyl ester (145385-46-2) → Nα,Nα'-<3-hydroxy-3-tert-(tert-butoxycarbonyl)glutaryl>bisε-cinnamoyl-Nε-(benzoyloxy)-L-lysine methyl ester> (145385-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 0.5 h / 0 °C

2: 28 percent / 1) diphenyl phosphorazidate, 2) Et₃N / 1) DMF, 0 deg C, 10 min, 2) DMF, a) 0 deg C, 3 h, b) to r.t., overnight

With diphenyl phosphoryl azide; triethylamine;

DOI:10.1021/jo00052a030

upstream raw materials:

3-(tert-butoxycarbonyl)-3-hydroxypentanedioic acid

N-α-(tert-butoxycarbonyl)-L-lysine methyl ester

N^ε-cinnamoyl-N^ε-(benzoyloxy)-N^α-BOC-L-lysine methyl ester

dibenzoyl peroxide

Downstream raw materials:

nannochelin A

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