(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

Base Information

• Chemical Name: (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
• CAS No.: 476622-81-8
• Molecular Formula: C₃₆H₆₀O₆Si
• Molecular Weight: 616.954
• Mol file: 476622-81-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 31 articles about (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 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: 97.0%

(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 (476622-80-7) → (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 (476622-81-8)

Guidance literature:

(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; With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In benzene; at 20 ℃; for 13h;

With dmap; In benzene; at 20 ℃; for 4h; Further stages.;

DOI:10.1021/ja020853m

Reference yield:

methyl (6S)-(E)-6,7-dihydroxy-5-methyl-3-heptenoate → (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 (476622-81-8)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 °C

2.1: O₃; pyridine / methanol / -78 °C

2.2: 91 percent / Me₂S / methanol / 4 h / 20 °C

3.1: TiCl₄ / CH₂Cl₂ / 49 h / -78 - -30 °C

4.1: O₃; pyridine / methanol / -78 °C

4.2: Me₂S / methanol / 6 h / 20 °C

5.1: 89 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 26 h / -20 - 0 °C

6.1: 89 percent / CSA / 12 h / 20 °C

7.1: 96 percent / HF*py; pyridine / tetrahydrofuran / 3.67 h / 0 - 20 °C

8.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2.67 h / 0 - 20 °C

9.1: CH₂Cl₂; diethyl ether / 0.25 h / -78 °C

10.1: 516 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

11.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

11.2: 88 percent / tetrahydrofuran; toluene / 1 h / -78 °C

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

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

12.3: 82 percent / Pd(PPh₃)4; LiCl / tetrahydrofuran; pentane / -78 - 0 °C

13.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

14.1: 73 percent / DIBAL / CH₂Cl₂; hexane / 7 h / 20 °C

15.1: 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical; NaOCl; NaHCO₃ / KBr / CH₂Cl₂; H₂O / 0.33 h / 0 °C

16.1: 97 percent / NaClO₂; NaH₂PO₄; 2-methylbutene / 2-methyl-propan-2-ol; H₂O

17.1: 2,4,6-trichlorobenzoyl chloride; i-Pr₂NEt / benzene / 13 h / 20 °C

17.2: 97 percent / DMAP / benzene / 4 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; titanium tetrachloride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical; pyridine hydrogenfluoride; ozone; 2-Methyl-1-butene; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; potassium bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetic acid; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene;

DOI:10.1021/ja020853m

Reference yield:

(4R,5R,6S)-6,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3,5-dimethyl-heptan-2-one → (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 (476622-81-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 89 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 26 h / -20 - 0 °C

2.1: 89 percent / CSA / 12 h / 20 °C

3.1: 96 percent / HF*py; pyridine / tetrahydrofuran / 3.67 h / 0 - 20 °C

4.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2.67 h / 0 - 20 °C

5.1: CH₂Cl₂; diethyl ether / 0.25 h / -78 °C

6.1: 516 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

7.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

7.2: 88 percent / tetrahydrofuran; toluene / 1 h / -78 °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

11.1: 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical; NaOCl; NaHCO₃ / KBr / CH₂Cl₂; H₂O / 0.33 h / 0 °C

12.1: 97 percent / NaClO₂; NaH₂PO₄; 2-methylbutene / 2-methyl-propan-2-ol; H₂O

13.1: 2,4,6-trichlorobenzoyl chloride; i-Pr₂NEt / benzene / 13 h / 20 °C

13.2: 97 percent / DMAP / benzene / 4 h / 20 °C

With pyridine; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical; pyridine hydrogenfluoride; 2-Methyl-1-butene; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; potassium bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetic acid; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene;

DOI:10.1021/ja020853m

upstream 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

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