(3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

Base Information

• Chemical Name: (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• CAS No.: 26048-05-5
• Molecular Formula: C45H57N3O9
• Molecular Weight: 783.962
• Hs Code.: 29419090
• UNII: 26S048LS2R
• DSSTox Substance ID: DTXSID00891834
• Nikkaji Number: J21.174E
• Wikipedia: Beauvericin
• NCI Thesaurus Code: C1011
• Metabolomics Workbench ID: 52995
• ChEMBL ID: CHEMBL249052
• Mol file: 26048-05-5.mol

Synonyms:beauvericin

Chemical Property of (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 93-94℃
• Refractive Index: 1.529
• Boiling Point: 975.6 °C at 760 mmHg
• PKA: -1.02±0.70(Predicted)
• Flash Point: 543.8 °C
• PSA: 139.83000
• Density: 1.126 g/cm³
• LogP: 4.72620
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (30 mg/ml)
• XLogP3: 8.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 783.40948040
• Heavy Atom Count: 57
• Complexity: 1200

Purity/Quality:

98% ^*data from raw suppliers

Beauvericin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)O1)CC2=CC=CC=C2)C)C(C)C)CC3=CC=CC=C3)C)C(C)C)CC4=CC=CC=C4)C
• Isomeric SMILES: CC(C)[C@@H]1C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O1)CC2=CC=CC=C2)C)C(C)C)CC3=CC=CC=C3)C)C(C)C)CC4=CC=CC=C4)C
• Description: Beauvericin (CAS 26048-05-5) induces apoptosis in A549 cancer cells.1 Disrupts mitochondrial volume regulation.2 Antifungal activity acting via inhibition of both multidrug efflux and TORC1 kinase.3 Crosses the blood-brain barrier in mice.4 Inhibits HIV-1 integrase.5
• Uses: Beauvericin is a cyclic depsipeptide isolated from several fungal genera, notably Beauveria and Fusarium, first reported in 1969. Beauvericin exhibits broad antifungal, antibacterial, antiprotozoan and insecticidal activities. At the molecular level, beauvericin exhibits ionophoric properties, and inhibits acyl-CoA:cholesterol acyltransferase activity. Beauvericin induces apoptosis by elevating intracellular calcium levels. Toxic depsipeptide with antibiotic and insecticidal effects.Beauvericin is a toxic depsipeptide with antibiotic and insecticidal effects.

Technology Process of (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

There total 13 articles about (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone 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:

C45H58ClN3O9 → beauvericin (26048-05-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 18.5h; Inert atmosphere;

DOI:10.1002/chem.201504457

Reference yield:

(R)-2-Hydroxy-3-methylbutyric acid (17407-56-6) → beauvericin (26048-05-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / 0 °C / Inert atmosphere

1.2: 15 h / 0 - 20 °C / Inert atmosphere

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

5.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

7.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

8.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere

9.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; dmap; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; palladium 10% on activated carbon; hydrogen; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201504457

Reference yield:

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) → beauvericin (26048-05-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sulfuric acid; sodium nitrite / water / 60 °C / 5171.62 Torr / Inert atmosphere

2.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / 0 °C / Inert atmosphere

2.2: 15 h / 0 - 20 °C / Inert atmosphere

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

5.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

7.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

8.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere

9.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; dmap; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; sulfuric acid; palladium 10% on activated carbon; hydrogen; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201504457

upstream raw materials:

(R)-2-Hydroxy-3-methylbutyric acid

D-Val-OH

benzyl (R)-2-hydroxy-3-methylbutanoate

Downstream raw materials:

C₄₅H₅₇N₃O₉*Na⁽¹⁺⁾

Refernces