(12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal

Base Information

• Chemical Name: (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal
• CAS No.: 308357-92-8
• Molecular Formula: C₄₇H₇₉NO₆SSi₂
• Molecular Weight: 842.384

Synonyms:(12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal

Chemical Property of (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal

Chemical Property:

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Technology Process of (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal

There total 24 articles about (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-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:

(3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-1-hydroxy-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one (308357-91-7) → (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal (308357-92-8)

Guidance literature:

With Dess-Martin periodane; In pyridine; dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo0007480

Reference yield:

4-(chloromethyl)-2-methyl-1,3-thiazole (39238-07-8) → (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal (308357-92-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 97 percent / benzene / 8 h / Heating

2.1: KHMDS / tetrahydrofuran / 0.75 h / -78 °C

2.2: 86 percent / tetrahydrofuran / 0.33 h / 40 °C

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

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

4.2: tetrahydrofuran / 0.5 h / -78 °C

5.1: 98 percent / DIBALH / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

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

7.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -78 °C

7.2: 77 percent / tetrahydrofuran / 0.5 h / -100 °C

8.1: 70 percent / Mg; HgCl₂; MeOH / ethanol / 2 h / 40 - 50 °C

9.1: 98 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

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

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

11.2: 1.66 g / tetrahydrofuran; various solvent(s) / 0.33 h / -90 °C

12.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -15 °C

13.1: 98 percent / CSA / methanol; CH₂Cl₂ / 5 h / 0 °C

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

With 1H-imidazole; 2,6-dimethylpyridine; methanol; 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; acetonitrile; benzene; 2.2: Wittig olefination / 3.1: Swern oxidation / 4.2: Wadsworth-Horner-Emmons olefination;

DOI:10.1021/jo0007480

Reference yield:

(-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate (198768-47-7) → (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal (308357-92-8)

Guidance literature:

Multi-step reaction with 15 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

6.1: 98 percent / DIBALH / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

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

8.1: 18-crown-6; KHMDS / tetrahydrofuran / 0.25 h / -78 °C

8.2: 77 percent / tetrahydrofuran / 0.5 h / -100 °C

9.1: 70 percent / Mg; HgCl₂; MeOH / ethanol / 2 h / 40 - 50 °C

10.1: 98 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

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

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

12.2: 1.66 g / tetrahydrofuran; various solvent(s) / 0.33 h / -90 °C

13.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -15 °C

14.1: 98 percent / CSA / methanol; CH₂Cl₂ / 5 h / 0 °C

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

With 1H-imidazole; 2,6-dimethylpyridine; methanol; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; triphenylphosphine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; acetonitrile; 2.2: Wittig olefination / 4.1: Swern oxidation / 5.2: Wadsworth-Horner-Emmons olefination;

DOI:10.1021/jo0007480

upstream raw materials:

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

4-(chloromethyl)-2-methyl-1,3-thiazole

(-)-(5S)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-4,4-dimethylheptan-3-one

(-)-(3S)-3-[(4-methoxybenzyl)oxy]dihydrofuran-2(3H)-one

Downstream raw materials:

(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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