1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

Base Information

• Chemical Name: 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol
• CAS No.: 167893-00-7
• Molecular Formula: C₃₉H₆₄F₆O₄Si₂
• Molecular Weight: 767.096
• Mol file: 167893-00-7.mol

Synonyms:1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

Chemical Property of 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

There total 10 articles about 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol 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: 82.0%

Hexafluoroacetone (684-16-2) + 1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene (167892-99-1) → 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol (167893-00-7)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -70 ℃; for 0.5h;

DOI:10.1016/S0968-0896(00)00106-1

Reference yield:

(5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene (143884-26-8) → 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol (167893-00-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

2: 92 percent / NMO; 4 Angstroem MS / tetrapropylammonium perrutenate / CH₂Cl₂ / 0.25 h / 20 °C

3: 82 percent / LiN(TMS)2 / tetrahydrofuran / 0.5 h / -70 °C

With N-methyl-2-indolinone; 4 Angstroem MS; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Grignard reaction / 2: Oxidation / 3: Condensation;

DOI:10.1016/S0968-0896(00)00142-5

Reference yield:

(R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol (167892-98-0) → 1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol (167893-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / NMO; 4 Angstroem MS / tetrapropylammonium perrutenate / CH₂Cl₂ / 0.25 h / 20 °C

2: 82 percent / LiN(TMS)2 / tetrahydrofuran / 0.5 h / -70 °C

With N-methyl-2-indolinone; 4 Angstroem MS; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane; 1: Oxidation / 2: Condensation;

DOI:10.1016/S0968-0896(00)00142-5

upstream raw materials:

Hexafluoroacetone

1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene

(5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene

(R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol

Downstream raw materials:

1α,3β-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-trien-23(R),25-diol

ST₂₃₂

1α,3β-bis[(t-butyldimethylsilyl)oxy]-23(R),25-epoxy-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-triene

1α,3β-bis[(t-butyldimethylsilyl)oxy]-23(S),25-epoxy-26,26,26,27,27,27-hexafluoro-9,10-secocholesta-5(Z),7(E),10(19)-triene