(3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone

Base Information

• Chemical Name: (3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone
• CAS No.: 83597-45-9
• Molecular Formula: C₄₄H₄₈N₄O₁₀
• Molecular Weight: 792.886

Synonyms:(3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone

Chemical Property of (3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone

Chemical Property:

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Technology Process of (3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone

There total 4 articles about (3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone 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: 8.78%

N,N'-bis[(1S)-1-benzyl-2-hydroxyethyl]diglycolyldiamide (83597-41-5) + N,N'-3-oxa-pentanoyl-(S,S)-diphenylalanine (83597-43-7) → (3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone (83597-45-9)

Guidance literature:

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 0 ℃; for 14h;

Reference yield:

(S)-2-{2-[((S)-1-Ethoxycarbonyl-2-phenyl-ethylcarbamoyl)-methoxy]-acetylamino}-3-phenyl-propionic acid ethyl ester (83597-39-1) → (3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone (83597-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80.7 percent / LiAlH₄ / tetrahydrofuran / 3 h / -50 °C

2: 8.78 percent / N,N'-carbonyldiimidazole / tetrahydrofuran / 14 h / 0 °C

With lithium aluminium tetrahydride; 1,1'-carbonyldiimidazole; In tetrahydrofuran;

Reference yield:

(L)-phenylalanine ethyl ester hydrochloride (3182-93-2) → (3S,11S,15S,23S)-3,11,15,23-Tetrabenzyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,9,12,17,21-hexaone (83597-45-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) TDI; 2.) Et₃N / 1.) THF, 30 min, RT, futher reag.; 2.) 20 h, RT

2: 87.8 percent / LiAlH₄ / tetrahydrofuran / -30 °C

3: 1.) CDI / 1.) THF, 1 h; 2.) DMF, THF, 20 h, RT

With lithium aluminium tetrahydride; triethylamine; 1,1'-carbonyldiimidazole; 2,4-Toluene diisocyanate; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)86893-9

upstream raw materials:

N,N'-bis[(1S)-1-benzyl-2-hydroxyethyl]diglycolyldiamide

N,N'-3-oxa-pentanoyl-(S,S)-diphenylalanine

H-Phe-OEt

(S)-2-{2-[((S)-1-Ethoxycarbonyl-2-phenyl-ethylcarbamoyl)-methoxy]-acetylamino}-3-phenyl-propionic acid ethyl ester

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