(3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-diol

Base Information

• Chemical Name: (3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-diol
• CAS No.: 872221-82-4
• Molecular Formula: C₂₉H₄₃NO₆SSi₂
• Molecular Weight: 589.901
• Mol file: 872221-82-4.mol

Synonyms:(3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-diol

Chemical Property of (3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-diol

There total 2 articles about (3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-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: 85.0%

(3aS,3bR,9bR,10R,11S,11aS)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-11-(tert-butyldimethylsilyloxy)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridin-10-ol (872221-81-3) → (3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-diol (872221-82-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

DOI:10.1021/ol052372o

Reference yield:

(3aS,3bR,9bR,10R,11S,11aS)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-10-phenylcarbonyloxy-11-(tert-butyldimethylsilyloxy)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine (872221-80-2) → (3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-diol (872221-82-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / sodium methoxide / methanol / 0.17 h / 20 °C

2: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

With tetrabutyl ammonium fluoride; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1139/V06-078

Reference yield: 79.0%

(3aS,3bR,9bR,10R,11S,11aR)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine-10,11-diol (872221-82-4) → (1S,2S,3S,4S,4aR,10bR)-5-(4-methylphenylsulfonyl)-8,9-di(trimethylsilyl)-1,2,3,4,4a,5,6,10b-octahydro-1,2,3,4-phenanthridinetetraol

Guidance literature:

With Dowex 50WX₈-100; water; In methanol; at 70 ℃; for 4h;

DOI:10.1021/ol052372o

upstream raw materials:

(3aS,3bR,9bR,10R,11S,11aS)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-11-(tert-butyldimethylsilyloxy)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridin-10-ol

(3aS,3bR,9bR,10R,11S,11aS)-2,2-dimethyl-4-(4-methylphenylsulfonyl)-10-phenylcarbonyloxy-11-(tert-butyldimethylsilyloxy)-7,8-di(trimethylsilyl)-3a,3b,4,5,9b,10,11,11a-octahydro[1,3]dioxolo[4,5-c]phenanthridine