(-)-(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

Base Information

• Chemical 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
• CAS No.: 218614-16-5
• Molecular Formula: C19H33NO2SSi
• Molecular Weight: 367.628
• Mol file: 218614-16-5.mol

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

Chemical Property of (-)-(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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 58-60°C
• Boiling Point: 450.692°C at 760 mmHg
• Flash Point: 226.37°C
• PSA: 70.59000
• Density: 1.019g/cm³
• LogP: 5.57390
• Solubility.: Acetone, Chloroform, Ethanol, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

(-)-(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 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(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

There total 14 articles about (-)-(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 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: 99.0%

4-[(1E,5Z)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-hepta-1,5-dienyl]-2-methyl-thiazole (220889-40-7) → (-)-(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)

Guidance literature:

With ammonium chloride; magnesium bromide; In diethyl ether;

DOI:10.1021/jo982108r

Reference yield: 98.0%

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) → (-)-(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)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at 0 ℃; for 2.5h;

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

Reference yield:

(Z)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-7-(tetrahydro-pyran-2-yloxy)-hept-5-en-2-one (220889-39-4) → (-)-(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)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

2.1: 99 percent / Mg; 1,2-dibromoethane / diethyl ether / 3.5 h / 20 °C

With n-butyllithium; magnesium; ethylene dibromide; In tetrahydrofuran; diethyl ether; hexane; 1.2: Wadsworth-Emmons olefination;

DOI:10.1021/ja010454b

upstream raw materials:

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

4-[(1E,5Z)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-7-(tetrahydro-pyran-2-yloxy)-hepta-1,5-dienyl]-2-methyl-thiazole

(Z)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-7-(tetrahydro-pyran-2-yloxy)-hept-5-en-2-one

2-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enethioic acid S-ethyl ester

Downstream raw materials:

(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

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

(2S,6Z,9S,10E)-1,9-Bis[(1,1-dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-diene

(2S,6Z,9S,10E)-9-[(1,1-Dimethylethyl)dimethylsilyloxy]-11-(2-methylthiazol-4-yl)-2,6,10-trimethyl-undeca-6,10-dien-1-ol

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