(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

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-dien-1-ol
CAS No.:308357-87-1
Molecular Formula:C₂₆H₃₇NO₃S
Molecular Weight:443.651
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-dien-1-ol

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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-dien-1-ol

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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-dien-1-ol

There total 14 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-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: 98.0%

: 308357-86-0
4-{(1E,3S,5Z,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethylundeca-1,5-dienyl}-2-methyl-1,3-thiazole

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1021/jo0007480

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

: 308357-87-1
(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

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; methanol; 18-crown-6 ether; tetrabutyl ammonium fluoride; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; magnesium; triphenylphosphine; mercury dichloride; In tetrahydrofuran; diethyl ether; ethanol; 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

: 308357-87-1
(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

Guidance literature:: Multi-step reaction with 3 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

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