(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

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Chemical Name:(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid
CAS No.:308357-93-9
Molecular Formula:C₄₇H₇₉NO₇SSi₂
Molecular Weight:858.384
Hs Code.:

(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

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Chemical Property of (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

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Technology Process of (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

There total 27 articles about (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid 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: 92.0%

: (12Z,16E)-(3S,8S,15S)-1,3,7-Tris-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one

: 308357-93-9
(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

Guidance literature:: (12Z,16E)-(3S,8S,15S)-1,3,7-Tris-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one; With pyridine; hydrogen fluoride;

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

: 308357-93-9
(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

Guidance literature:: Multi-step reaction with 11 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

7.1: LDA / tetrahydrofuran; various solvent(s) / 1 h / -78 - -15 °C

7.2: 1.66 g / tetrahydrofuran; various solvent(s) / 0.33 h / -90 °C

8.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -15 °C

9.1: 98 percent / CSA / methanol; CH₂Cl₂ / 5 h / 0 °C

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

11.1: 74 mg / NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O; various solvent(s) / 2 h

With 1H-imidazole; 2,6-dimethylpyridine; methanol; sodium chlorite; sodium dihydrogenphosphate; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; triphenylphosphine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;
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

: 308357-93-9
(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

Guidance literature:: Multi-step reaction with 9 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

5.1: LDA / tetrahydrofuran; various solvent(s) / 1 h / -78 - -15 °C

5.2: 1.66 g / tetrahydrofuran; various solvent(s) / 0.33 h / -90 °C

6.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -15 °C

7.1: 98 percent / CSA / methanol; CH₂Cl₂ / 5 h / 0 °C

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

9.1: 74 mg / NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O; various solvent(s) / 2 h

With 2,6-dimethylpyridine; methanol; sodium chlorite; sodium dihydrogenphosphate; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; magnesium; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo0007480