(E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone

Base Information

• Chemical Name: (E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone
• CAS No.: 321983-72-6
• Molecular Formula: C₃₀H₄₄N₄O₅
• Molecular Weight: 540.703
• Mol file: 321983-72-6.mol

Synonyms:(E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone

Chemical Property of (E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone

There total 14 articles about (E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone 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: 60.0%

hept-6-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester (321983-71-5) → (E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone (321983-72-6)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane;

DOI:10.1021/ja021327y

Reference yield:

(tert-butoxycarbonyl)-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic asid methyl ester (247186-16-9) → (E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone (321983-72-6)

Guidance literature:

Multi-step reaction with 5 steps

1: TFA / CH₂Cl₂ / 2 h / 0 °C

2: tetrahydrofuran

3: aq. LiOH / tetrahydrofuran

4: 60 percent / Ph₃P; DEAD / tetrahydrofuran

5: 60 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂

With lithium hydroxide; Grubbs catalyst first generation; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 4: Mitsunobu reaction;

DOI:10.1021/ja021327y

Reference yield:

(S)-1-[(S)-2-((S)-2-Hept-6-enoylamino-3-methyl-butyrylamino)-3-phenyl-propionyl]-hexahydro-pyridazine-3-carboxylic acid → (E)-(3S,6S,21S)-3-benzyl-6-isopropyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]-pentacos-13-ene-2,5,8,20-tetraone (321983-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / Ph₃P; DEAD / tetrahydrofuran

2: 60 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂

With Grubbs catalyst first generation; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1: Mitsunobu reaction;

DOI:10.1021/ja021327y

upstream raw materials:

hept-6-en-1-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid hex-5-enyl ester

hept-6-enoic acid

(tert-butoxycarbonyl)-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic asid methyl ester

hept-6-en-oyl-L-valine-L-phenylalanine-hexahydropyridazine-3S-carboxylic acid methyl ester

Refernces

• 1、 Wagner,Cabrejas,Grossmith,Papageorgiou,Senia,Wagner,France,Nolan. "Synthesis of macrolide analogues of sanglifehrin by RCM: Unique reactivity of a Ruthenium carbene complex bearing an Imidazol-2-ylidene ligand". . p. 9255 - 9260. Retrieved 2007/10/03.