(2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

Base Information

Chemical Name:(2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal
CAS No.:308357-89-3
Molecular Formula:C₂₆H₃₅NO₃S
Molecular Weight:441.635
Hs Code.:

Synonyms:(2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

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Chemical Property of (2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

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Technology Process of (2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

There total 15 articles about (2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal 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:

: 308357-87-1
(2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dien-1-ol

: 308357-89-3
(2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

Guidance literature:: DOI:10.1007/s007060070099

Reference yield:

: 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

: 308357-89-3
(2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / DIBALH / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

2.1: Ph₃P; imidazole; I₂ / acetonitrile; diethyl ether / 0.5 h / 20 °C

3.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -78 °C

3.2: 77 percent / tetrahydrofuran / 0.5 h / -100 °C

4.1: 70 percent / Mg; HgCl₂; MeOH / ethanol / 2 h / 40 - 50 °C

5.1: 98 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂; pyridine / 2 h / 20 °C

With 1H-imidazole; methanol; 18-crown-6 ether; tetrabutyl ammonium fluoride; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; triphenylphosphine; mercury dichloride; In tetrahydrofuran; pyridine; diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jo0007480

Reference yield:

: 4-{(1E,3S,5Z)-7-iodo-3-[(4-methoxybenzyl)oxy]-2,6-dimethyl-hepta-1,5-dienyl}-2-methyl-1,3-thiazole

: 308357-89-3
(2S,6Z,9S,10E)-9-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

Guidance literature:: Multi-step reaction with 4 steps

1.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -78 °C

1.2: 77 percent / tetrahydrofuran / 0.5 h / -100 °C

2.1: 70 percent / Mg; HgCl₂; MeOH / ethanol / 2 h / 40 - 50 °C

3.1: 98 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂; pyridine / 2 h / 20 °C

With methanol; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; magnesium; mercury dichloride; In tetrahydrofuran; pyridine; ethanol; dichloromethane;
DOI:10.1021/jo0007480