(5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-25-ol

Base Information

• Chemical Name: (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-25-ol
• CAS No.: 303015-21-6
• Molecular Formula: C₄₁H₆₈F₆O₅Si₂
• Molecular Weight: 811.149

Synonyms:(5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-25-ol

Chemical Property of (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-25-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-25-ol

There total 5 articles about (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-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: 97.0%

acetic anhydride (108-24-7) + 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 (167893-02-9) → (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatrien-25-ol (303015-21-6)

Guidance literature:

In pyridine; at 20 ℃; for 12h;

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

Reference yield:

(5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene (143884-26-8) → (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatrien-25-ol (303015-21-6)

Guidance literature:

Multi-step reaction with 5 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

4: 52 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / -10 °C

5: 97 percent / pyridine / 12 h / 20 °C

With sodium tetrahydroborate; N-methyl-2-indolinone; 4 Angstroem MS; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; 1: Grignard reaction / 2: Oxidation / 3: Condensation / 4: Reduction / 5: Acetylation;

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) → (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatrien-25-ol (303015-21-6)

Guidance literature:

Multi-step reaction with 4 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

3: 52 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / -10 °C

4: 97 percent / pyridine / 12 h / 20 °C

With sodium tetrahydroborate; N-methyl-2-indolinone; 4 Angstroem MS; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; dichloromethane; 1: Oxidation / 2: Condensation / 3: Reduction / 4: Acetylation;

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

upstream raw materials:

acetic anhydride

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

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

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

Downstream raw materials:

Falecalcitriol

(6Z)-(3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5⁽¹⁰⁾,6,8-cholestatriene-3,25-diol-1-one

(6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol

(5Z,7E)-(1S,3R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10⁽¹⁹⁾-cholestatriene

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