4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)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)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole
CAS No.:308357-85-9
Molecular Formula:C₄₈H₅₉NO₅S₂Si
Molecular Weight:822.218
Hs Code.:

4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole

Synonyms:4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole

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Chemical Property of 4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole

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Technology Process of 4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole

There total 17 articles about 4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)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: 85.0%

: 263900-30-7
(-)-(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutyl phenyl sulfone

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

: 308357-85-9
4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole

Guidance literature:: DOI:10.1007/s007060070099

Reference yield: 77.0%

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

: C₂₇H₃₃LiO₃SSi

: 308357-85-9
4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole

Guidance literature:: C₂₇H₃₃LiO₃SSi; In tetrahydrofuran; at -78 ℃; for 1h;

4-{(1E,3S,5Z)-7-iodo-3-[(4-methoxybenzyl)oxy]-2,6-dimethyl-hepta-1,5-dienyl}-2-methyl-1,3-thiazole; In tetrahydrofuran; for 1h; Further stages.;
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

: 308357-85-9
4-[(1E,3S,5Z,8R/S,10S)-11-{[tert-butyl(diphenyl)silyl]oxy}-3-[(4-methoxybenzyl)oxy]-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; 18-crown-6 ether; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; acetonitrile;
DOI:10.1021/jo0007480