8,13-Hexadecadien-3-ol, 5,11-bis[(4-methoxyphenyl)methoxy]-2,4,10,12-tetramethyl-16-[(2S,3R, 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,3R, 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.: 565229-55-2
• Molecular Formula: C47H73NO10
• Molecular Weight: 812.097
• Mol file: 565229-55-2.mol

Synonyms:

Chemical Property of 8,13-Hexadecadien-3-ol, 5,11-bis[(4-methoxyphenyl)methoxy]-2,4,10,12-tetramethyl-16-[(2S,3R, 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,3R, 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 31 articles about 8,13-Hexadecadien-3-ol, 5,11-bis[(4-methoxyphenyl)methoxy]-2,4,10,12-tetramethyl-16-[(2S,3R, 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%

(1S,2S,3R,6Z,8S,9S,10S,11Z)-5,11-bis(4-methoxybenzyloxy)-16-[(2R,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4,10,12-tetramethylhexadeca-8,13-dien-3-ol (565229-92-7) + Trichloroacetyl isocyanate (3019-71-4) → carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-1-isopropyl-3,9-bis(4-methoxybenzyloxy)-14-[(2R,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,8,10-trimethyltetradeca-6,11-dienyl ester (565229-55-2)

Guidance literature:

(1S,2S,3R,6Z,8S,9S,10S,11Z)-5,11-bis(4-methoxybenzyloxy)-16-[(2R,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4,10,12-tetramethylhexadeca-8,13-dien-3-ol; Trichloroacetyl isocyanate; In dichloromethane; at 20 ℃;

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1021/jm0204136

Reference yield:

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2-methyl-hexanal (565229-01-8) → carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-1-isopropyl-3,9-bis(4-methoxybenzyloxy)-14-[(2R,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,8,10-trimethyltetradeca-6,11-dienyl ester (565229-55-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: Bu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

1.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

1.3: 2.29 g / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / pH 7.0

2.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / Heating

3.1: 83 percent / HF*pyridine; pyridine / methanol / 48 h / 20 °C

4.1: diisobutylaluminum hydride / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

5.1: pyridinium p-toluenesulfonate / 15 h / 20 °C

6.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure

7.1: 274 mg / Dess-Martin periodinane / CH₂Cl₂ / 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: 267 mg / Dess-Martin periodinane / CH₂Cl₂

11.1: NaHMDS / tetrahydrofuran / 20 °C

11.2: tetrahydrofuran / -78 - 20 °C

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

13.1: Dess-Martin periodinane / CH₂Cl₂

14.1: 65 percent / tetrahydrofuran / 0 - 20 °C

15.1: CH₂Cl₂ / 20 °C

15.2: 72 percent / K₂CO₃ / methanol / 20 °C

With pyridine; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; 7.1: Dess-Martin oxidation / 8.2: Wittig olefination / 10.1: Dess-Martin oxidation / 11.2: Wittig olefination / 13.1: Dess-Martin oxidation;

DOI:10.1021/jm0204136

Reference yield:

(3R,4S,5R,6S)-6-[3-(4-Methoxy-benzyloxy)-propyl]-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-ol → carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-1-isopropyl-3,9-bis(4-methoxybenzyloxy)-14-[(2R,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,8,10-trimethyltetradeca-6,11-dienyl ester (565229-55-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridinium p-toluenesulfonate / 15 h / 20 °C

2.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure

3.1: 274 mg / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

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

4.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

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

6.1: 267 mg / Dess-Martin periodinane / CH₂Cl₂

7.1: NaHMDS / tetrahydrofuran / 20 °C

7.2: tetrahydrofuran / -78 - 20 °C

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

9.1: Dess-Martin periodinane / CH₂Cl₂

10.1: 65 percent / tetrahydrofuran / 0 - 20 °C

11.1: CH₂Cl₂ / 20 °C

11.2: 72 percent / K₂CO₃ / methanol / 20 °C

With hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 3.1: Dess-Martin oxidation / 4.2: Wittig olefination / 6.1: Dess-Martin oxidation / 7.2: Wittig olefination / 9.1: Dess-Martin oxidation;

DOI:10.1021/jm0204136

upstream raw materials:

(1S,2S,3R,6Z,8S,9S,10S,11Z)-5,11-bis(4-methoxybenzyloxy)-16-[(2R,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4,10,12-tetramethylhexadeca-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

Downstream raw materials:

Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester