Epothilone A

Base Information

Chemical Name:Epothilone A
CAS No.:152044-53-6
Molecular Formula:C26H39NO6S
Molecular Weight:493.665
Hs Code.:
NSC Number:684362
UNII:51E07YBX96
DSSTox Substance ID:DTXSID10332288
Nikkaji Number:J1.408.121F
Wikidata:Q27104197
NCI Thesaurus Code:C1622
Metabolomics Workbench ID:21312
ChEMBL ID:CHEMBL329993
Mol file:152044-53-6.mol

Synonyms:epothilon A;epothilone A

Suppliers and Price of Epothilone A

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Epothilone A
100ug
$ 513.00

TRC
EpothiloneA
1mg
$ 110.00

Sigma-Aldrich
(?)-Epothilone A fromSorangiumcellulosum,>95%(HPLC),solid
10 μg
$ 213.00

Sigma-Aldrich
(?)-Epothilone A from
10ug
$ 205.00

DC Chemicals
EpothiloneA >98%
250 mg
$ 1500.00

DC Chemicals
EpothiloneA >98%
1 g
$ 3000.00

Crysdot
(-)-EpothiloneA 97%
25mg
$ 245.00

Crysdot
(-)-EpothiloneA 97%
10mg
$ 126.00

Crysdot
(-)-EpothiloneA 97%
5mg
$ 70.00

ChemScene
EpothiloneA 99.75%
25mg
$ 320.00

Total 49 raw suppliers

Chemical Property of Epothilone A

Chemical Property:

Vapor Pressure:1.31E-19mmHg at 25°C
Melting Point:95 °C
Refractive Index:1.531
Boiling Point:683.317 °C at 760 mmHg
PKA:13.57±0.70(Predicted)
Flash Point:367.057 °C
PSA：137.49000
Density:1.143 g/cm³
LogP:4.08740
Storage Temp.:?20°C
Solubility.:Chloroform (Slightly), Ethyl Acetate (Slightly)
XLogP3:4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:2
Exact Mass:493.24980914
Heavy Atom Count:34
Complexity:770

Purity/Quality:

99%, ^*data from raw suppliers

Epothilone A ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: Total 1 MSDS from other Authors

Useful:

Canonical SMILES:CC1CCCC2C(O2)CC(OC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C
Isomeric SMILES:C[C@H]1CCC[C@@H]2[C@@H](O2)C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)C)/C
General Description (-)-EPOTHILONE A is a structurally complex polyketide macrolide with potent anticancer activity, functioning as a microtubule-stabilizing agent akin to taxol. It has been synthesized through stereocontrolled and enantioselective methods, including nitrile oxide cycloadditions, aldol couplings, and multifunctional asymmetric catalysis, highlighting its significance as a target for synthetic and medicinal chemistry. These synthetic approaches underscore its potential as a therapeutic agent and the advancement of methodologies for constructing intricate natural products.

Technology Process of Epothilone A

There total 262 articles about Epothilone A 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: 93.0%

: 479485-03-5
(1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-11-hydroxy-7-(4-methoxybenzyloxy)-8,8,10,12-tetramethyl-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

: 152044-53-6
epithilone A

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/1521-3765(20020816)8:16<3717::AID-CHEM3717>3.0.CO;2-G

Reference yield: 65.0%

: 186692-73-9
desoxyepothilone A

: 152044-53-6
epithilone A

Guidance literature:: With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃;
DOI:10.1021/ja971110h

Reference yield: 60.0%

: 186692-73-9
desoxyepothilone A

: 152044-53-6
epithilone A

: 193071-75-9
[1R,3S,7S,10R,11S,12S,16S]-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-[2-methylthiazol-4-yl]prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Guidance literature:: With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃;
DOI:10.1021/ja971109i

upstream raw materials:

desoxyepothilone A

(7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

(1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-11-hydroxy-7-(4-methoxybenzyloxy)-8,8,10,12-tetramethyl-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

(4S,7R,8S,16S)-8-hydroxy-4-(4-methoxybenzyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxacyclohexadec-13-en-2,6-dione

Downstream raw materials:

desoxyepothilone A

[4S-[4R*,7S*,8R*,9R*,13R*,14R*,16R*(E)]]-14-Azido-5,5,7,9-tetramethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-13-[(4-nitrobenzoyl)oxy]-4,8-bis [(triethylsilyl)oxy]-1-oxacyclohexadecane-2,6-dione

epothilone E

Refernces

Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies

10.1021/jo015791h

The research describes a concise and stereocontrolled total synthesis of epothilone A and a formal synthesis of epothilone B, which are structurally unique polyketide macrolides with significant anticancer activity. The synthesis routes leverage nitrile oxide cycloadditions and a highly diastereoselective convergent aldol coupling, resulting in the expeditious construction of these complex molecules with complete stereocontrol. Key chemicals used in the process include isoxazolines, allylic alcohols, phosphonates, and various reagents for selective oxidations, reductions, and protection/deprotection steps. The study not only achieves the synthesis of epothilones A and B but also contributes to the advancement of novel methodologies for carbon-carbon bond formation and the development of scalable approaches to these important natural products.

Enantioselective total synthesis of epothilone A using multifunctional asymmetric catalyses

10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

The research focuses on the enantioselective total synthesis of epothilone A, a potent antitumor agent that stabilizes microtubules, similar to taxol. The purpose of the study was to achieve this synthesis using simple asymmetric catalysts, which had not been accomplished at the time. The researchers successfully utilized multifunctional asymmetric catalyses, including direct aldol reactions and cyanosilylation, to synthesize epothilone A. The conclusions of the research were that the enantioselective total synthesis of epothilone A was achieved, marking a significant advancement in the field of organic synthesis, particularly for the synthesis of complex molecules with potential medicinal applications.

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