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26048-05-5

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Basic Information
CAS No.: 26048-05-5
Name: Beauvericin
Article Data: 1
Molecular Structure:
Molecular Structure of 26048-05-5 (Beauvericin)
Formula: C45H57N3O9
Molecular Weight: 783.962
Synonyms: Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl];
Density: 1.126 g/cm3
Melting Point: 93-94℃
Boiling Point: 975.6 °C at 760 mmHg
Flash Point: 543.8 °C
PSA: 139.83000
LogP: 4.72620
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Synthetic route

Boc-Me-Phe-D-Hiv-Me-Phe-D-Hiv-Me-Phe-D-Hiv-OBn

26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
2: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
3: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
17407-56-6

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

26048-05-5

beauvericin

Conditions
ConditionsYield
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
View Scheme
Multi-step reaction with 11 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: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
4.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
6.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
8.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
9.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
10.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 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: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
4.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
6.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
7.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
8.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
640-68-6

D-Val-OH

26048-05-5

beauvericin

Conditions
ConditionsYield
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
View Scheme
Multi-step reaction with 11 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: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
6.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
8.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
9.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
10.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 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 / 17 h / 0 - 20 °C / Inert atmosphere
7.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
9.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
10.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
11.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
12.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
2441-07-8, 65138-05-8, 14487-24-2

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

26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere
2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
3: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
5: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
7: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
8: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
9: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere
2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
3: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
5: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
6: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
7: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
8: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere
2: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C / Inert atmosphere
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
4: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
6: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
7: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
8: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
9: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme

C22H27NO4*ClH

26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
2: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
4: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
5: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
6: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme

C20H29NO6

26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
4: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
5: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
3: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
5: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
6: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
7: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
8: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme

C37H46N2O7*(x)ClH

26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
3: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
4: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme

C50H67N3O12

26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
2: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme

C45H59N3O10

26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme

C20H28ClNO5

26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
2: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
3: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
4: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
2: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
4: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere
5: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere
6: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
7: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
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Specification

The CAS registry number of Beauvericin is 26048-05-5. It belongs to the product category of Peptide. This chemical is also named as Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl]. In addition, its molecular formula is C45H57N3O9 and molecular weight is 783.95. Its systematic name and IUPAC name are the same which is called 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.

Physical properties about Beauvericin are: (1)ACD/LogP: 5.49; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 5.49; (4)ACD/LogD (pH 7.4): 5.49; (5)ACD/BCF (pH 5.5): 8794.53; (6)ACD/BCF (pH 7.4): 8794.54; (7)ACD/KOC (pH 5.5): 23166.35; (8)ACD/KOC (pH 7.4): 23166.35; (9)#H bond acceptors: 12; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 9; (12)Index of Refraction: 1.529; (13)Molar Refractivity: 214.85 cm3; (14)Molar Volume: 695.8 cm3; (15)Surface Tension: 40.5 dyne/cm; (16)Density: 1.126 g/cm3; (17)Flash Point: 543.8 °C; (18)Enthalpy of Vaporization: 142.33 kJ/mol; (19)Boiling Point: 975.6 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1N(C)C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC1C(C)C)Cc2ccccc2)C)C(C)C)Cc3ccccc3)C)C(C)C)Cc4ccccc4
(2)InChI: InChI=1/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3
(3)InChIKey: GYSCAQFHASJXRS-UHFFFAOYAE