(2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol

Base Information

• Chemical Name: (2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol
• CAS No.: 251099-51-1
• Molecular Formula: C₃₆H₆₂O₆Si
• Molecular Weight: 618.97
• Mol file: 251099-51-1.mol

Synonyms:(2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol

Chemical Property of (2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol

There total 32 articles about (2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol 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: 98.0%

(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane (251099-50-0) → (2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol (251099-51-1)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1021/ja992370x

Reference yield:

(2S,3R,4S)-3,5-O-[bis-(1,1-dimethylethyl)silylene]-2,4-dimethylpropionaldehyde (184528-56-1) → (2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol (251099-51-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 87 percent / TiCl₄ / CH₂Cl₂ / -78 - -30 °C

2.1: HF*pyridine; pyridine / tetrahydrofuran / 1 h / 0 °C

3.1: 2.29 g / imidazole / dimethylformamide / 4 h / 20 °C

4.1: 99 percent / p-toluenesulfonic acid monohydrate / 0.75 h / 20 °C

5.1: O₃; pyridine / methanol / -78 °C

5.2: Me₂S / methanol / 4 h / -78 - 20 °C

6.1: 1.09 g / NaBH₄ / methanol / 0.5 h / 0 °C

7.1: 98 percent / I₂; triphenylphosphine; imidazole / CH₂Cl₂ / 12.25 h / 0 - 20 °C

8.1: t-BuLi / pentane / 0.5 h / -78 - 20 °C

8.2: ZnCl₂ / tetrahydrofuran; pentane / 0.25 h / -78 °C

8.3: 82 percent / Pd(PPh₃)4; LiCl / tetrahydrofuran; pentane / -78 - 0 °C

9.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; titanium tetrachloride; pyridine hydrogenfluoride; ozone; triphenylphosphine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ja020853m

Reference yield:

(3E,5S,6S,7R,8R,9S)-(E)-8,10-O-[bis-(1,1-dimethylethyl)silylene]-6-hydroxy-5,7,9-trimethyldec-3-enoic acid methyl ester (184758-35-8) → (2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11,13-((R)-benzylidenedioxy)-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-ol (251099-51-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: HF*pyridine; pyridine / tetrahydrofuran / 1 h / 0 °C

2.1: 2.29 g / imidazole / dimethylformamide / 4 h / 20 °C

3.1: 99 percent / p-toluenesulfonic acid monohydrate / 0.75 h / 20 °C

4.1: O₃; pyridine / methanol / -78 °C

4.2: Me₂S / methanol / 4 h / -78 - 20 °C

5.1: 1.09 g / NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 98 percent / I₂; triphenylphosphine; imidazole / CH₂Cl₂ / 12.25 h / 0 - 20 °C

7.1: t-BuLi / pentane / 0.5 h / -78 - 20 °C

7.2: ZnCl₂ / tetrahydrofuran; pentane / 0.25 h / -78 °C

7.3: 82 percent / Pd(PPh₃)4; LiCl / tetrahydrofuran; pentane / -78 - 0 °C

8.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; pyridine hydrogenfluoride; ozone; triphenylphosphine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ja020853m

upstream raw materials:

(2R,3S,4S,5R,6S,9S,10S,11R,12R,13S)-6-(tert-butyldimethylsiloxy)-14-((tert-butyldiphenylsiloxy))-2,4-((R)-benzylidenedioxy)-10,12-(isopropylidenedioxy)-7-methylene-3,5,9,11,13-pentamethyltetradecane

benzaldehyde dimethyl acetal

(2S,3S)-3,4-(di(tert-butyldimethylsilyloxy))-2-methyl-butanal

(5R,6S,7S)-(E)-methyl-8-[(tert-butyldiphenylsilyl)oxy]-6-hydroxy-5,7-dimethyl-3-octenoate

Downstream raw materials:

(2S,3R,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11-benzyloxy-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1,13-diol

(2R,3S,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11-benzyloxy-13-hydroxy-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1-al

(2R,3S,4R,5S,6S,9S,10R,11S,12R,13R)-9-(tert-butyldimethylsiloxy)-11-benzyloxy-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12,13-hexamethyltetradecanolide

(2R,3S,4R,5S,6S,9S,10R,11S,12S,13R)-9-(tert-butyldimethylsiloxy)-11-benzyloxy-13-hydroxy-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecanoic acid