186692-73-9

Basic information

• Product Name: Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-
• Synonyms: Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-;(4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione;Epo C;4,8-dihydroxy-5,5,7,9-tetramethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
• CAS NO: 186692-73-9
• Molecular Formula: C₂₆H₃₉NO₅S
• Molecular Weight: 477.66
• Mol File: 186692-73-9.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 657.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.097
• PKA: 13.47±0.70(Predicted)
• CAS DataBase Reference: Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-(186692-73-9)
• EPA Substance Registry System: Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-(186692-73-9)

Safety Data

• Hazardous Substances Data: 186692-73-9(Hazardous Substances Data)

Usage

Uses

Epothilone C is a related compound of Epothilones, which are a novel class of antineoplastic agents with antitubulin activity. In addition, Epothilones utilize a similar mechanism of action to that of taxanes and are less susceptible to multidrug resistance caused by P-glycoprotein. Studies showed that Epothilones exhibit antitumor activity against human cancer cells that are taxane-resistant.

Upstream product

• 204194-92-3 (4S,7R,8S,9S,16S)-4,8-Di-tert-butyldimethylsilyloxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecen-2,6-dione 
• 20949-84-2 2-methylthiazole-4-carbaldehyde 
• 188899-09-4 (3S,6R,7S,8S)-3,7-Di-(tert-butyldimethylsilyloxy)-1-hydroxy-4,4,6,8-tetramethyl-12-tridecen-5-one 
• 187283-43-8 (5S)-5-hydroxy-4,4-dimethyloct-7en-3-one 
• 187283-44-9 (5S)-5-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyloct-7en-3-one 
• 193146-29-1 (3S)-3-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-5-oxo-heptanal 
• 250679-53-9 (5S)-5-{[(tert-butyl)dimethylsilyl]oxy}-7-hydroxy-4,4-dimethylheptan-3-one 
• 186692-84-2 (4S,7R,8S,9S,16S)-4,8-bis-(tert-butyldimethylsilanyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-vinyl]-(13Z)-1-oxacyclohexadec-13-ene-2,6-dione 
• 188259-76-9 (1S)-1-[(E)-1-Methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-3-butenyl (3S,6R,7S,8S)-3,7-di-[tert-butyldimethylsilyloxy]-4,4,6,8-tetramethyl-5-oxo-12-tridecenoate 
• 331268-23-6 (S)-5-((tert-butyldimethylsilyl)oxy)-4,4-dimethyl-7-((triethylsilyl)oxy)heptan-3-one 
• 188730-11-2 4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole 
• 188729-99-9 [(S)-6-benzyloxy-2-methyl-hexyloxy]-tert-butyl-dimethyl-silane 
• 188729-96-6 (S)-6-Benzyloxy-2-methyl-hexanal 
• 188729-97-7 (S)-6-benzyloxy-2-methyl-1-hexanol 

Downstream Products

• 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 
• 298200-29-0 [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 

Relevant articles and documents

Synthesis, structure proof, and biological activity of epothilone cyclopropanes.

[structure--see text] A semisynthetic route to epothilone cyclopropanes from epothilones A and B is described. Of significance, the deoxygenation of the 12, 13-epoxide to give the corresponding olefin was achieved with high efficiency. The title compounds (8, 9) were active in both tubulin polymerization and cytotoxicity assays, which is in direct contrast to a previously published report. These results provide further evidence that the role of the 12,13-epoxide of epothilones is largely conformational and argue against some of the current pharmacophore models.

Concise total syntheses of epothilone A and C based on alkyne metathesis

A ring closing alkyne metathesis reaction catalyzed by the molybdenum complex 26 followed by a Lindlar reduction of the resulting cycloalkyne product opens an efficient and stereoselective entry into epothilone A and C.

Total synthesis of epothilone A: The macrolactonization approach

This highly convergent and practical total synthesis of the antitumor agent epothilone A uses a macrolactonization as the key step. The strategy may provide access to a variety of epothilones desirable for biological screening.

Z-SELECTIVE RING-CLOSING METATHESIS REACTIONS

The present invention relates generally to olefin metathesis. In some embodiments, the present invention provides methods for Z-selective ring-closing metathesis.

A total synthesis of epothilones using solid-supported reagents and scavengers

A total synthesis of epothilone C(1) with concomitant formal synthesis of epothilone A is described, using immobilized reagents and scavengers to effect multistep synthetic transformations and purifications.