(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

Base Information

• Chemical Name: (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
• CAS No.: 476622-78-3
• Molecular Formula: C₃₆H₆₄O₆Si
• Molecular Weight: 620.986
• Mol file: 476622-78-3.mol

Synonyms:(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

Chemical Property of (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

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-benzyloxy-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1,13-diol

There total 28 articles about (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 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: 73.0%

(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) → (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 (476622-78-3)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at 20 ℃; for 7h;

DOI:10.1021/ja020853m

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-benzyloxy-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1,13-diol (476622-78-3)

Guidance literature:

Multi-step reaction with 10 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

10.1: 73 percent / DIBAL / CH₂Cl₂; hexane / 7 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; titanium tetrachloride; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; triphenylphosphine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; 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-benzyloxy-3,5-(isopropylidenedioxy)-8-methylene-2,4,6,10,12-pentamethyltetradecan-1,13-diol (476622-78-3)

Guidance literature:

Multi-step reaction with 9 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

9.1: 73 percent / DIBAL / CH₂Cl₂; hexane / 7 h / 20 °C

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

DOI:10.1021/ja020853m

upstream raw materials:

(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

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:

(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

(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-pentamethyltetradecan-1-al