ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)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-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate
CAS No.:198768-52-4
Molecular Formula:C₂₃H₂₉NO₄S
Molecular Weight:415.554
Hs Code.:

Synonyms:ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

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Chemical Property of ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

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Technology Process of ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

There total 8 articles about ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)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: 80.0%

: 107905-52-2
ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate

: 1027920-39-3
(3S,4E)-3-[(4-methoxybenzyl)oxy]-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al

: 198768-52-4
ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

: ethyl (2E,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h; Yields of byproduct given;
DOI:10.1016/S0040-4039(97)10150-2

Reference yield:

: 198768-54-6
(3S,4E)-3-[(4-methoxybenzyl)oxy]-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol

: 198768-52-4
ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin periodinane / CH₂Cl₂; pyridine / 0.25 h / 20 °C

2.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.42 h / -78 °C

2.2: tetrahydrofuran / 0.5 h / -78 °C

With 18-crown-6 ether; potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; pyridine; dichloromethane; 1.1: Swern oxidation / 2.2: Wadsworth-Horner-Emmons olefination;
DOI:10.1021/jo0007480

Reference yield:

: 198768-47-7
(-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate

: 198768-52-4
ethyl (2Z,5S,6E)-5-[(4-methoxybenzyl)oxy]-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / tetrahydrofuran; diethyl ether / 1.5 h / -100 °C

2.1: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C

2.2: 74 percent / tetrahydrofuran / 1 h / 40 - 50 °C

3.1: DIBALH / CH₂Cl₂; various solvent(s) / 5 h / -20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂; pyridine / 0.25 h / 20 °C

5.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.42 h / -78 °C

5.2: tetrahydrofuran / 0.5 h / -78 °C

With 18-crown-6 ether; sodium hexamethyldisilazane; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; 2.2: Wittig olefination / 4.1: Swern oxidation / 5.2: Wadsworth-Horner-Emmons olefination;
DOI:10.1021/jo0007480