218614-16-5

Basic information

• Product Name: (-)-(2Z,5S,6E)-5-{[tert-Butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol
• Synonyms: (-)-(2Z,5S,6E)-5-{[tert-Butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol;(2Z,5S,6E)-5-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-2,6-diMethyl-7-(2-Methyl-4-thiazolyl)-2,6-heptadien-1-ol
• CAS NO: 218614-16-5
• Molecular Formula: C₁₉H₃₃NO₂SSi
• Molecular Weight: 367.62132
• Product Categories: Chiral Reagents
• Mol File: 218614-16-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 58-60°C
• Boiling Point: 450.692°C at 760 mmHg
• Flash Point: 226.37°C
• Appearance: /
• Density: 1.019g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.526
• Solubility: Acetone, Chloroform, Ethanol, Methanol
• CAS DataBase Reference: (-)-(2Z,5S,6E)-5-{[tert-Butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(2Z,5S,6E)-5-{[tert-Butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol(218614-16-5)
• EPA Substance Registry System: (-)-(2Z,5S,6E)-5-{[tert-Butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dien-1-ol(218614-16-5)

Safety Data

• Hazardous Substances Data: 218614-16-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C19H33NO2SSi/c1-14(12-21)9-10-18(22-24(7,8)19(4,5)6)15(2)11-17-13-23-16(3)20-17/h9,11,13,18,21H,10,12H2,1-8H3/b14-9-,15-11+/t18-/m0/s1

Upstream product

• 218614-04-1 ethyl (2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate 
• 220889-40-7 4-[(1E,5Z)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-hepta-1,5-dienyl]-2-methyl-thiazole 
• 220889-39-4 (Z)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-7-(tetrahydro-pyran-2-yloxy)-hept-5-en-2-one 
• 220889-37-2 2-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enethioic acid S-ethyl ester 
• 220889-33-8 (S)-4-Benzyl-3-[(Z)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoyl]-oxazolidin-2-one 
• 220889-34-9 (S)-4-Benzyl-3-[(Z)-(S)-2-hydroxy-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoyl]-oxazolidin-2-one 
• 220889-35-0 (S)-4-Benzyl-3-[(Z)-(S)-2-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoyl]-oxazolidin-2-one 
• 39238-07-8 4-(chloromethyl)-2-methyl-1,3-thiazole 
• 164264-14-6 (3S)-3-[(1,1-Dimethylethyl)dimethylsilyloxy]-oxolan-2-one 
• 188899-14-1 (3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol 
• 188730-08-7 (3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al 
• 218615-21-5 (3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxypentan-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 152044-54-7 epothilone B 
• 189453-10-9 epothilone D 
• 189453-35-8 (4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione 
• 193146-53-1 (5S,8R,9S,10S,17S,Z)-9-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,10,14,19,19,20,20-tridecamethyl-17-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,18-dioxa-3,19-disilahenicos-14-en-7-one 
• 193146-51-9 (7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-49-5 (7S,10R,11S,12S,19S,Z)-7-(tert-butyldimethylsilyloxy)-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-63-3 (12Z,16E)-(3S,6R,7S,8S,15S)-3,7,15-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid 
• 193146-26-8 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid 
• 210690-99-6 (2S,6Z,9S,10E)-9-[(1,1-Dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-dien-1-ol 
• 210690-85-0 (2S,6Z,9S,10E)-1,9-Bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-diene 
• 308357-81-5 4-[(1E,3S,5Z,8R/S,10S)-3,11-bis{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole 
• 263900-31-8 (2S,4R,6Z,9S,10E)-1,9-Bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-4-phenylsulfonyl-2,6,10-trimethyl-undeca-6,10-diene 

Relevant articles and documents

THIA-EPOTHILONE DERIVATIVES FOR THE TREATMENT OF CANCER

The present invention relates to new Macrocycles of formula (I) and their use for the treatment of cancer.

Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D

The phosphonium salt 35, representing one of the two principal subunits of the epothilones, was prepared from propargyl alcohol via heptenone 22. A Wittig reaction of the phosphorane from 35 with aldehyde 33, obtained from aldol condensation of ketone 27 with aldehyde 28, afforded 37. Seco acid 42 derived from 37 underwent lactonization to give cis-9,10-dehydroepothilone D (43) which was selectively reduced with diimide to yield epothilone D (4) and, after epoxidation, epothilone B (2). An alternative route to epothilone D employed alkyne 39, obtained from 33, in a Castro-Stephens reaction with allylic bromide 34 to furnish enyne 40. The latter was semi-hydrogenated to provide 37. Alkyne 46, prepared from alcohol 45, was converted to trans-vinylstannane 47 which, in a Stille coupling with allylic chloride 50, gave 51. Seco acid 52 derived from 51 underwent lactonization to give trans-9,10-dehydroepothilone D (54). Bioassay data comparing the antiproliferative activity and tubulin polymerization of 43 and 54 with epothilone B (2), epothilone D (4), and paclitaxel (7) showed that the synthetic analogues were less potent than their natural counterparts, although both retain full antiproliferative activity against a paclitaxel-resistant cell line. No significant difference in potency was noted between cis analogue 43 and its trans isomer 54.

A highly stereoselective synthesis of epothilone B

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