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26048-05-5

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26048-05-5 Usage

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

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 26048-05-5 differently. You can refer to the following data:
1. 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.
2. Toxic depsipeptide with antibiotic and insecticidal effects.Beauvericin is a toxic depsipeptide with antibiotic and insecticidal effects.

Definition

ChEBI: A trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues.

References

1) Lu et al. (2016), Beauvericin-induced cell apoptosis through the mitogen-activated protein kinase pathway in human nonsmall cell lung cancer A549 cells.; J. Toxicol. Sci., 41 429 2) Tonshin et al. (2010), The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis.; Toxicology, 276 49 3) Shekhar-Guturja et al. (2016), Dual action antifungal small molecule modulates multidrug efflux and TOR signaling; Nat. Chem. Biol., 12 867 4) Taevernier et al. (2016), Blood-brain barrier transport kinetics of the cyclic depsipeptide mycotoxins beauvericin and enniatins; Toxicol. Lett., 258 175 5) Shin et al. (2009), Beauvericin and enniatins H,I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase; J. Antibiot. (Tokyo), 62 687

Check Digit Verification of cas no

The CAS Registry Mumber 26048-05-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,0,4 and 8 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 26048-05:
(7*2)+(6*6)+(5*0)+(4*4)+(3*8)+(2*0)+(1*5)=95
95 % 10 = 5
So 26048-05-5 is a valid CAS Registry Number.
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/t34-,35-,36-,37+,38+,39+/m0/s1

26048-05-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Beauvericin

1.2 Other means of identification

Product number -
Other names beauverin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:26048-05-5 SDS

26048-05-5Synthetic route

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

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

beauvericin
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
(R)-2-Hydroxy-3-methylbutyric acid
17407-56-6

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

beauvericin
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
D-Val-OH
640-68-6

D-Val-OH

beauvericin
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
benzyl (R)-2-hydroxy-3-methylbutanoate
2441-07-8, 65138-05-8, 14487-24-2

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

beauvericin
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

C22H27NO4*ClH

beauvericin
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

C20H29NO6

beauvericin
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

C37H46N2O7*(x)ClH

beauvericin
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

C50H67N3O12

beauvericin
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

C45H59N3O10

beauvericin
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

C20H28ClNO5

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

Boc-Me-Phe-D-Hiv-OBn

beauvericin
26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
2: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °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
Multi-step reaction with 8 steps
1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °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
Multi-step reaction with 9 steps
1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
2: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °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
C45H58ClN3O9

C45H58ClN3O9

beauvericin
26048-05-5

beauvericin

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 18.5h; Inert atmosphere;46 mg
Boc-Me-Phe-D-Hiv-Me-Phe-D-Hiv-OBn

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

beauvericin
26048-05-5

beauvericin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °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
beauvericin
26048-05-5

beauvericin

C45H57N3O9*Na(1+)
1398380-27-2

C45H57N3O9*Na(1+)

Conditions
ConditionsYield
With sodium picrate In water; nitrobenzene at 25℃; for 2h;

26048-05-5Downstream Products

26048-05-5Relevant articles and documents

Synthesis of Natural and Unnatural Cyclooligomeric Depsipeptides Enabled by Flow Chemistry

Lücke, Daniel,Dalton, Toryn,Ley, Steven V.,Wilson, Zoe E.

, p. 4206 - 4217 (2016/03/16)

Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b). A reliable flow chemistry protocol was established for the coupling and macrocyclisation to form challenging N-methylated amides. This flexible approach has allowed the rapid synthesis of both natural and unnatural depsipeptides in high yields, enabling further exploration of their promising biological activity. Harnessing technology: Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b), resulting in increased overall yields, while decreasing the effort required for the researcher.

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