2,6-Heptadienoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-methyl-7-(2-methyl-4-thiazolyl)- , ethyl ester, (2E,5S,6E)-

Base Information

Chemical Name:2,6-Heptadienoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-methyl-7-(2-methyl-4-thiazolyl)- , ethyl ester, (2E,5S,6E)-
CAS No.:849418-98-0
Molecular Formula:C30H37NO3SSi
Molecular Weight:519.78
Hs Code.:

Synonyms:

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Chemical Property of 2,6-Heptadienoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-methyl-7-(2-methyl-4-thiazolyl)- , ethyl ester, (2E,5S,6E)-

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Technology Process of 2,6-Heptadienoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-methyl-7-(2-methyl-4-thiazolyl)- , ethyl ester, (2E,5S,6E)-

There total 6 articles about 2,6-Heptadienoic acid, 5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-methyl-7-(2-methyl-4-thiazolyl)- , ethyl ester, (2E,5S,6E)- 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: 28.0%

: (2-methyl-thiazol-4-ylmethyl)-phosphonic acid dimethyl ester

: 849418-96-8
ethyl (2E)(5S)-5-tert-butyldiphenylsilyloxy-6-oxohept-2-enoate

: 849418-98-0
ethyl (2E,6E)(5S)-5-tert-butyldiphenylsilyloxy-6-methyl-7-{2-methyl-(1,3-thiazol-4-yl)}hepta-2,6-dienoate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 11h; Horner-Wadsworth-Emmons olefination;
DOI:10.3987/COM-04-S(P)30

Reference yield:

: 119729-76-9
ethyl (2E)(5S)-5-tert-butyldiphenylsilyloxy-6-hydroxyhex-2-enoate

: 849418-98-0
ethyl (2E,6E)(5S)-5-tert-butyldiphenylsilyloxy-6-methyl-7-{2-methyl-(1,3-thiazol-4-yl)}hepta-2,6-dienoate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

2: 44 percent / tetrahydrofuran; hexane; diethyl ether / 12 h / -78 - 20 °C

3: 88 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

4: 28 percent / n-BuLi / hexane; tetrahydrofuran / 11 h / -78 - 20 °C / Horner-Wadsworth-Emmons olefination

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1: Swern oxidation / 3: Swern oxidation;
DOI:10.3987/COM-04-S(P)30

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 849418-98-0
ethyl (2E,6E)(5S)-5-tert-butyldiphenylsilyloxy-6-methyl-7-{2-methyl-(1,3-thiazol-4-yl)}hepta-2,6-dienoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

2.1: DIBAL / CH₂Cl₂ / 0.5 h / 20 °C

2.2: 78 percent / CH₂Cl₂ / 12 h / 20 °C

3.1: 100 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

4.1: 44 percent / tetrahydrofuran; hexane; diethyl ether / 12 h / -78 - 20 °C

5.1: 88 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

6.1: 28 percent / n-BuLi / hexane; tetrahydrofuran / 11 h / -78 - 20 °C / Horner-Wadsworth-Emmons olefination

With 1H-imidazole; n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 3.1: Swern oxidation / 5.1: Swern oxidation;
DOI:10.3987/COM-04-S(P)30