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

Base Information

• Chemical Name: (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10⁽¹⁹⁾-cholestatriene
• CAS No.: 303015-22-7
• Molecular Formula: C₄₃H₇₂F₆O₆Si₂
• Molecular Weight: 855.202

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

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

Chemical Property:

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

There total 6 articles about (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10⁽¹⁹⁾-cholestatriene 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: 89.0%

chloromethyl methyl ether (107-30-2) + (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) → (5Z,7E)-(1S,3R,23R)-23-acetoxy-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10(19)-cholestatriene (303015-22-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In chloroform; for 1h; Heating;

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-25-methoxymethoxy-9,10-seco-5,7,10(19)-cholestatriene (303015-22-7)

Guidance literature:

Multi-step reaction with 6 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

6: 89 percent / iPr₂NEt / CHCl₃ / 1 h / Heating

With sodium tetrahydroborate; N-methyl-2-indolinone; 4 Angstroem MS; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; 1: Grignard reaction / 2: Oxidation / 3: Condensation / 4: Reduction / 5: Acetylation / 6: Alkylation;

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-25-methoxymethoxy-9,10-seco-5,7,10(19)-cholestatriene (303015-22-7)

Guidance literature:

Multi-step reaction with 5 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

5: 89 percent / iPr₂NEt / CHCl₃ / 1 h / Heating

With sodium tetrahydroborate; N-methyl-2-indolinone; 4 Angstroem MS; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; 1: Oxidation / 2: Condensation / 3: Reduction / 4: Acetylation / 5: Alkylation;

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

upstream raw materials:

chloromethyl methyl ether

(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

(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:

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

(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

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

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

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