10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-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: 10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-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.: 81418-10-2
• Molecular Formula: C₃₃H₄₂O₇SSi
• Molecular Weight: 610.844
• Mol file: 81418-10-2.mol

Synonyms:10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-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 10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-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 10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-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 10 articles about 10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-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: 88.0%

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) → 10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene (81418-10-2)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 25 ℃; for 1.5h;

DOI:10.1021/jo00167a020

Reference yield:

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

Guidance literature:

Multi-step reaction with 8 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

8: 88 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran; pyridine / 1.5 h / 25 °C

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

DOI:10.1021/jo00167a020

Reference yield:

2-acetoxy-3-(4'-methoxyphenylthio)-1,3-butadiene (65174-13-2) → 10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene (81418-10-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 88 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran; pyridine / 1.5 h / 25 °C

With boron trichloride; pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo00167a020

upstream raw materials:

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

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

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

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

Downstream raw materials:

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