8,13-Hexadecadien-3-ol, 5,11-bis[(4-methoxyphenyl)methoxy]-2,4,10,12-tetramethyl-16-[(2S,3S, 4S,5R,6R)-tetrahydro-6-methoxy-4-(methoxymethoxy)-3,5-dimethyl-2H- pyran-2-yl]-, carbamate, (3S,4S,5R,8Z,10S,11R,12S,13Z)-

Base Information

• Chemical Name: 8,13-Hexadecadien-3-ol, 5,11-bis[(4-methoxyphenyl)methoxy]-2,4,10,12-tetramethyl-16-[(2S,3S, 4S,5R,6R)-tetrahydro-6-methoxy-4-(methoxymethoxy)-3,5-dimethyl-2H- pyran-2-yl]-, carbamate, (3S,4S,5R,8Z,10S,11R,12S,13Z)-
• CAS No.: 565229-57-4
• Molecular Formula: C47H73NO10
• Molecular Weight: 812.097
• Mol file: 565229-57-4.mol

Synonyms:

Chemical Property of 8,13-Hexadecadien-3-ol, 5,11-bis[(4-methoxyphenyl)methoxy]-2,4,10,12-tetramethyl-16-[(2S,3S, 4S,5R,6R)-tetrahydro-6-methoxy-4-(methoxymethoxy)-3,5-dimethyl-2H- pyran-2-yl]-, carbamate, (3S,4S,5R,8Z,10S,11R,12S,13Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8,13-Hexadecadien-3-ol, 5,11-bis[(4-methoxyphenyl)methoxy]-2,4,10,12-tetramethyl-16-[(2S,3S, 4S,5R,6R)-tetrahydro-6-methoxy-4-(methoxymethoxy)-3,5-dimethyl-2H- pyran-2-yl]-, carbamate, (3S,4S,5R,8Z,10S,11R,12S,13Z)-

There total 26 articles about 8,13-Hexadecadien-3-ol, 5,11-bis[(4-methoxyphenyl)methoxy]-2,4,10,12-tetramethyl-16-[(2S,3S, 4S,5R,6R)-tetrahydro-6-methoxy-4-(methoxymethoxy)-3,5-dimethyl-2H- pyran-2-yl]-, carbamate, (3S,4S,5R,8Z,10S,11R,12S,13Z)- 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: 72.0%

(8Z,13Z)-(3S,4R,5R,10S,11R,12S)-5,11-Bis-(4-methoxy-benzyloxy)-16-((2S,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-2,4,10,12-tetramethyl-hexadeca-8,13-dien-3-ol (565229-93-8) + Trichloroacetyl isocyanate (3019-71-4) → carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-1-isopropyl-3,9-bis(4-methoxybenzyloxy)-14-[(2R,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,8,10-trimethyltetradeca-6,11-dienyl ester (565229-57-4)

Guidance literature:

(8Z,13Z)-(3S,4R,5R,10S,11R,12S)-5,11-Bis-(4-methoxy-benzyloxy)-16-((2S,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-2,4,10,12-tetramethyl-hexadeca-8,13-dien-3-ol; Trichloroacetyl isocyanate; In dichloromethane; at 20 ℃; for 0.5h;

With potassium carbonate; In methanol; at 20 ℃; for 3h;

DOI:10.1021/jm0204136

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-1-isopropyl-3,9-bis(4-methoxybenzyloxy)-14-[(2R,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,8,10-trimethyltetradeca-6,11-dienyl ester (565229-57-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 64 percent / pyridinium p-toluenesulfonate / benzene / 3 h / Heating

2.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: I₂; imidazole; triphenylphosphine / CH₂Cl₂ / 1 h / 0 °C

4.1: 4.5 g / benzene / 36 h / Heating

5.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

5.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

6.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

7.1: 270 mg / pyridinium sulfur trioxide; N,N-diisopropylethylamine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

8.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

8.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

9.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

10.1: Dess-Martin periodinane / CH₂Cl₂

11.1: 65 percent / tetrahydrofuran / 0 - 20 °C

12.1: CH₂Cl₂ / 0.5 h / 20 °C

12.2: 72 percent / K₂CO₃ / methanol / 3 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; benzene; 5.2: Wittig olefination / 8.2: Wittig olefination / 10.1: Dess-Martin oxidation;

DOI:10.1021/jm0204136

Reference yield:

(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one (154919-93-4) → carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-1-isopropyl-3,9-bis(4-methoxybenzyloxy)-14-[(2R,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,8,10-trimethyltetradeca-6,11-dienyl ester (565229-57-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / lithium borohydride / methanol; tetrahydrofuran / 2.33 h / 0 - 20 °C

2.1: 72 percent / pyridinium p-toluenesulfonate / benzene / 15 h / Heating

3.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: I₂; imidazole; triphenylphosphine / CH₂Cl₂ / 1 h / 0 °C

5.1: 4.5 g / benzene / 36 h / Heating

6.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

6.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

7.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

8.1: Dess-Martin periodinane / CH₂Cl₂

9.1: 65 percent / tetrahydrofuran / 0 - 20 °C

10.1: CH₂Cl₂ / 0.5 h / 20 °C

10.2: 72 percent / K₂CO₃ / methanol / 3 h / 20 °C

With 1H-imidazole; lithium borohydride; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene; 6.2: Wittig olefination / 8.1: Dess-Martin oxidation;

DOI:10.1021/jm0204136

upstream raw materials:

(8Z,13Z)-(3S,4R,5R,10S,11R,12S)-5,11-Bis-(4-methoxy-benzyloxy)-16-((2S,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-2,4,10,12-tetramethyl-hexadeca-8,13-dien-3-ol

Trichloroacetyl isocyanate

p-Anisaldehyde dimethyl acetal

(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one