218614-04-1

Basic information

• Product Name: 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
• Synonyms: 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;(2Z,5S,6E)-5-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-2,6-diMethyl-7-(2-Methyl-4-thiazolyl)-2,6-heptadienoic Acid Ethyl Ester
• CAS NO: 218614-04-1
• Molecular Formula: C21H35NO3SSi
• Molecular Weight: 409.658
• Product Categories: Chiral Reagents
• Mol File: 218614-04-1.mol

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Ether, Hexane, Methanol
• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(218614-04-1)
• EPA Substance Registry System: 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(218614-04-1)

Safety Data

• Hazardous Substances Data: 218614-04-1(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
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 is used as a synthetic intermediate for the development of various organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable asset in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 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 is used as a key building block for the synthesis of novel drug candidates. Its structural diversity and reactivity enable the development of new molecules with potential therapeutic applications, such as antibiotics, antivirals, and anticancer agents.
3. Used in Agrochemical Industry:
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 is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique chemical properties allow for the development of innovative compounds with improved efficacy, selectivity, and environmental compatibility.
4. Used in Specialty Chemicals Industry:
In the specialty chemicals industry, 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 is employed as a starting material for the synthesis of various specialty chemicals, such as dyes, fragrances, and additives. Its versatility and reactivity contribute to the development of new products with enhanced performance and application potential.

Upstream product

• 188899-14-1 (3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol 
• 107905-52-2 ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate 
• 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 
• 39238-07-8 4-(chloromethyl)-2-methyl-1,3-thiazole 
• 164264-14-6 (3S)-3-[(1,1-Dimethylethyl)dimethylsilyloxy]-oxolan-2-one 
• 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 
• 189453-35-8 (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 
• 189453-10-9 epothilone D 
• 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 
• 218614-16-5 (-)-(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 

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.

Method for producing epothilone B and derivatives, and intermediate products for this method

The invention relates to a method for producing epothilone B and derivatives, and to intermediate products for this method. According to the novel method, the epothilone B or derivatives are produced in high yields from the C1-C6, C7-C10 and C11-C20-fragm

Total Syntheses of Epothilones B and D

Total syntheses of the microtubule stabilizing antitumor drugs epothilone B and D are described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment D, and a sulfone anion allyl iodide alkylation to connect fragments B and C. Finally fragment D was attached to the B + C fragment via aldol addition.

Easy access to the epothilone family - Synthesis of epothilone B

An easy access to four out of five naturally occurring epothilones (A- E, 1-5) is reported. Key steps are an enantioselective Mukaiyama type aldol reaction, (E)- and (Z)-selective olefinations, and a sulfone alkylation.