2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene

Base Information

• Chemical Name: 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene
• CAS No.: 81418-09-9
• Molecular Formula: C₄₁H₅₈O₇SSi₂
• Molecular Weight: 751.144
• Mol file: 81418-09-9.mol

Synonyms:2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene

Chemical Property of 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene

There total 8 articles about 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene 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: 83.0%

2-acetoxy-3-(4'-methoxyphenylthio)-1,3-butadiene (65174-13-2) + 10-(tert-butyldimethylsiloxy)-8,9-(di-tert-butylsilylenedioxy)-1-oxo-1,4,4a(S*),9(R*),9a(R*),10(S*)-hexahydroanthracene (86668-46-4) → 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene (81418-09-9)

Guidance literature:

With boron trichloride; In dichloromethane; 1.) 1 h, -15 deg C, 2.) 2 h, 0 deg C;

DOI:10.1021/jo00167a020

Reference yield:

8-hydroxy-1-acetoxy-1(R*),4,4a(S*),9a(S*)-tetrahydroanthraquinone (86668-63-5) → 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene (81418-09-9)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄ / toluene; methanol / 0.12 h / 5 °C

2: 84 percent / 1-hydroxybenzotriazole, Et₃N / acetonitrile / 0.5 h / 65 °C / var. silyl transfer agents, without Et₃N, var. solv., var. temp., var. time

3: 59 percent / LiBH₄ / tetrahydrofuran / 48 h / 0 °C

4: 86 percent / imidazole / dimethylformamide / 6 h / 50 °C

5: 91 percent / diisobutylaluminum hydride / toluene; hexane / 0.5 h / -62 °C

6: 82 percent / Ac₂O / toluene / 20 h / 25 °C

7: 83 percent / 1 M BCl₃ / CH₂Cl₂ / 1.) 1 h, -15 deg C, 2.) 2 h, 0 deg C

With 1H-imidazole; sodium tetrahydroborate; lithium borohydride; acetic anhydride; boron trichloride; diisobutylaluminium hydride; benzotriazol-1-ol; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00167a020

Reference yield:

8,9-dihydroxy-1-acetoxy-10-oxo-1(R*),4,4a(S*),9(R*),9a(R*),10-hexahydroanthracene (1194750-34-9) → 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene (81418-09-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / 1-hydroxybenzotriazole, Et₃N / acetonitrile / 0.5 h / 65 °C / var. silyl transfer agents, without Et₃N, var. solv., var. temp., var. time

2: 59 percent / LiBH₄ / tetrahydrofuran / 48 h / 0 °C

3: 86 percent / imidazole / dimethylformamide / 6 h / 50 °C

4: 91 percent / diisobutylaluminum hydride / toluene; hexane / 0.5 h / -62 °C

5: 82 percent / Ac₂O / toluene / 20 h / 25 °C

6: 83 percent / 1 M BCl₃ / CH₂Cl₂ / 1.) 1 h, -15 deg C, 2.) 2 h, 0 deg C

With 1H-imidazole; lithium borohydride; acetic anhydride; boron trichloride; diisobutylaluminium hydride; benzotriazol-1-ol; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00167a020

upstream raw materials:

2-acetoxy-3-(4'-methoxyphenylthio)-1,3-butadiene

10-(tert-butyldimethylsiloxy)-8,9-(di-tert-butylsilylenedioxy)-1-oxo-1,4,4a(S*),9(R*),9a(R*),10(S*)-hexahydroanthracene

8-hydroxy-1-acetoxy-1(R*),4,4a(S*),9a(S*)-tetrahydroanthraquinone

8,9-dihydroxy-1-acetoxy-10-oxo-1(R*),4,4a(S*),9(R*),9a(R*),10-hexahydroanthracene

Downstream raw materials:

C₄₆H₆₈O₉SSi₂

C₄₄H₆₆O₈SSi₂

10,12-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-3-((4'-methoxyphenyl)thio)-11-oxo-1,4,4a(R*),5,5a(S*),6(S*),11,12a(S*)-octahydronaphthacene

10,11-dihydroxy-2-acetoxy-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,12,12a(S*)-hexahydronaphthacene