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

Base Information

• Chemical Name: 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
• CAS No.: 623927-01-5
• Molecular Formula: C₄₇H₆₈O₈
• Molecular Weight: 761.052
• Mol file: 623927-01-5.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 21 articles about 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 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:

pivaloyl chloride (3282-30-2) + 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) → 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 (623927-01-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 18h;

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) → 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 (623927-01-5)

Guidance literature:

Multi-step reaction with 10 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

10.1: pyridine / CH₂Cl₂ / 18 h / 20 °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) → 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 (623927-01-5)

Guidance literature:

Multi-step reaction with 9 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

9.1: pyridine / CH₂Cl₂ / 18 h / 20 °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:

pivaloyl chloride

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

(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