Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-6,11-dienyl ester

Base Information

• Chemical Name: Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-6,11-dienyl ester
• CAS No.: 623926-42-1
• Molecular Formula: C₄₂H₆₀O₇
• Molecular Weight: 676.934
• Mol file: 623926-42-1.mol

Synonyms:Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-6,11-dienyl ester

Chemical Property of Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-6,11-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-6,11-dienyl ester

There total 21 articles about Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-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: 84.0%

Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-15-(tetrahydro-pyran-2-yloxy)-pentadeca-6,11-dienyl ester (623926-41-0) → Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-6,11-dienyl ester (623926-42-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 55 ℃;

DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol (106296-58-6) → Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-6,11-dienyl ester (623926-42-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

2.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

2.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

3.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

4.1: 89 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: NaHMDS / tetrahydrofuran / 0.75 h / 20 °C

6.2: 0.214 g / tetrahydrofuran / -78 - 20 °C

7.1: 84 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

8.1: 95 percent / pyridine

9.1: 84 percent / PPTS / ethanol / 55 °C

With pyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; Dess-Martin periodane; ozone; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.2: Wittig reaction / 5.1: Dess-Martin oxidation / 6.2: Wittig reaction;

DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene (184291-95-0) → Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-15-hydroxy-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-pentadeca-6,11-dienyl ester (623926-42-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

1.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

2.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

2.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

3.1: 89 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: NaHMDS / tetrahydrofuran / 0.75 h / 20 °C

5.2: 0.214 g / tetrahydrofuran / -78 - 20 °C

6.1: 84 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

7.1: 95 percent / pyridine

8.1: 84 percent / PPTS / ethanol / 55 °C

With pyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; Dess-Martin periodane; ozone; In tetrahydrofuran; methanol; ethanol; dichloromethane; 2.2: Wittig reaction / 4.1: Dess-Martin oxidation / 5.2: Wittig reaction;

DOI:10.1016/S0968-0896(03)00186-X

upstream raw materials:

Acetic acid (6Z,11Z)-(1S,2S,3R,8S,9S,10S)-3,9-bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-15-(tetrahydro-pyran-2-yloxy)-pentadeca-6,11-dienyl ester

(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol

(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-enal

Downstream raw materials:

benzoic acid (Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-15-acetoxy-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester

acetic acid (Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-15-acetoxy-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester

2,2-dimethylpropionic acid (Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-15-acetoxy-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester