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

Base Information

• Chemical Name: 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
• CAS No.: 308357-81-5
• Molecular Formula: C36H61NO4S2Si2
• Molecular Weight: 692.188
• Mol file: 308357-81-5.mol

Synonyms: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;4-[(1E,3S,5Z,10S)-3,11-Bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-2,6,10-triMethyl-8-(phenylsulfonyl)-1,5-undecadi

Chemical Property of 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

Chemical Property:

• Vapor Pressure: 3.45E-18mmHg at 25°C
• Boiling Point: 691.6°C at 760 mmHg
• PKA: 2.72±0.10(Predicted)
• Flash Point: 372.1°C
• PSA: 102.11000
• Density: 1.027g/cm³
• LogP: 11.94300
• Solubility.: Chloroform, Dichloromethane, Ethanol, Ethyl Acetate, Methanol, Toluene

Purity/Quality:

95% ^*data from raw suppliers

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 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 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

There total 15 articles about 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 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: 93.0%

(-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone (218613-98-0) + 4-((1E,3S,5Z)-3-{[tert-butyl(dimethyl)silyl]oxy}-7-iodo-2,6-dimethylhepta-1,5-dienyl)-2-methyl-1,3-thiazole (218614-07-4) → 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 (308357-81-5)

Guidance literature:

(-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h;

4-((1E,3S,5Z)-3-{[tert-butyl(dimethyl)silyl]oxy}-7-iodo-2,6-dimethylhepta-1,5-dienyl)-2-methyl-1,3-thiazole; In tetrahydrofuran; at -78 ℃; for 1h; Further stages.;

DOI:10.1021/jo0007480

Reference yield:

(3S)-3-[(1,1-Dimethylethyl)dimethylsilyloxy]-oxolan-2-one (164264-14-6,669000-31-1) → 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 (308357-81-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 4.96 g / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

2.1: 10.95 g / LiHMDS / tetrahydrofuran / 0.67 h / 55 °C

3.1: oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / -78 - 20 °C

4.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h

4.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C

5.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C

6.1: Ph₃P; imidazole; I₂ / acetonitrile; diethyl ether / 1 h / 20 °C

7.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C

7.2: 93 percent / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; oxalyl dichloride; 18-crown-6 ether; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; acetonitrile; 2.1: Wittig olefination / 3.1: Swern oxidation / 4.2: Wittig olefination;

DOI:10.1021/jo0007480

Reference yield:

(3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol (188899-14-1) → 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 (308357-81-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / -78 - 20 °C

2.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h

2.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C

3.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C

4.1: Ph₃P; imidazole; I₂ / acetonitrile; diethyl ether / 1 h / 20 °C

5.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C

5.2: 93 percent / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; oxalyl dichloride; 18-crown-6 ether; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; acetonitrile; 1.1: Swern oxidation / 2.2: Wittig olefination;

DOI:10.1021/jo0007480

upstream raw materials:

(-)-(3S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutyl phenyl sulfone

4-((1E,3S,5Z)-3-{[tert-butyl(dimethyl)silyl]oxy}-7-iodo-2,6-dimethylhepta-1,5-dienyl)-2-methyl-1,3-thiazole

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

(3S)-3-methyl-1-phenylsulfonylbutan-4-ol

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

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