carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester

Base Information

• Chemical Name: carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester
• CAS No.: 565228-57-1
• Molecular Formula: C₄₉H₇₁NO₁₀
• Molecular Weight: 834.103
• Mol file: 565228-57-1.mol

Synonyms:carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester

Chemical Property of carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester

There total 39 articles about carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester 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: 68.0%

Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-14-((2S,3R,4S,5R,6R)-6-hydroxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester → carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester (565228-57-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 1h;

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)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester (565228-57-1)

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: 52 percent / NaHMDS / tetrahydrofuran / 4.33 h / -78 - 20 °C

12.1: tetrabutylammonium fluoride / tetrahydrofuran / 48 h / 20 °C

13.1: CH₂Cl₂ / 0.5 h / 20 °C

13.2: 72 percent / K₂CO₃ / methanol / 3 h / 20 °C

14.1: aq. AcOH / tetrahydrofuran / 4 h / 70 °C

15.1: 28.3 mg / Dess-Martin periodinane / CH₂Cl₂ / 1 h

With pyridine; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; 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 / 11.1: Wittig olefination / 15.1: Dess-Martin oxidation;

DOI:10.1021/jm0204136

Reference yield:

6-[(3R,4S,5S,6S)-3-(4-methoxybenzyloxy)propyl]-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-one (565229-05-2) → carbamic acid, (1S,2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-2,8,10-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyl ester (565228-57-1)

Guidance literature:

Multi-step reaction with 12 steps

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

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

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

4.1: 274 mg / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

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: 267 mg / Dess-Martin periodinane / CH₂Cl₂

8.1: 52 percent / NaHMDS / tetrahydrofuran / 4.33 h / -78 - 20 °C

9.1: tetrabutylammonium fluoride / tetrahydrofuran / 48 h / 20 °C

10.1: CH₂Cl₂ / 0.5 h / 20 °C

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

11.1: aq. AcOH / tetrahydrofuran / 4 h / 70 °C

12.1: 28.3 mg / Dess-Martin periodinane / CH₂Cl₂ / 1 h

With tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 4.1: Dess-Martin oxidation / 5.2: Wittig olefination / 7.1: Dess-Martin oxidation / 8.1: Wittig olefination / 12.1: Dess-Martin oxidation;

DOI:10.1021/jm0204136

upstream raw materials:

p-Anisaldehyde dimethyl acetal

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

(2S)-2-[(4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propan-1-ol

(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

Downstream raw materials:

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