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

Base Information

• Chemical 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
• CAS No.: 218614-04-1
• Molecular Formula: C21H35NO3SSi
• Molecular Weight: 409.665
• Mol file: 218614-04-1.mol

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

Chemical Property of 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

Chemical Property:

• PSA: 76.66000
• LogP: 6.14470
• Solubility.: Dichloromethane, Ether, Hexane, Methanol

Purity/Quality:

97% ^*data from raw suppliers

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 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 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# 218614-04-1) is a compound useful in organic synthesis.

Technology Process of 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

There total 9 articles about 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 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: 89.0%

(3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol (188899-14-1) + 2-[Bis-(2,2,2-trifluoro-ethyl)-phosphanyl]-propionic acid ethyl ester → 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)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0040-4039(98)02026-7

Reference yield:

(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al (188730-08-7) → 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)

Guidance literature:

bis-trifluoroethyl 2-ethoxy-2-oxo-1-methyl-ethylphosphonate; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.25h;

(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al; In tetrahydrofuran; toluene; at -78 ℃; for 2h;

Reference yield:

ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate (107905-52-2) + (3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al (188730-08-7) → 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)

Guidance literature:

ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; for 0.25h;

(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al; In tetrahydrofuran; at -78 ℃; for 0.5h; Further stages.;

DOI:10.1021/jo0007480

upstream raw materials:

(3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol

ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate

(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al

4-(chloromethyl)-2-methyl-1,3-thiazole

Downstream raw materials:

epothilone B

(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

epothilone D

(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