(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

Base Information

• Chemical Name: (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
• CAS No.: 303015-24-9
• Molecular Formula: C₄₃H₇₂F₆O₅S₂Si₂
• Molecular Weight: 903.335

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

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Technology Process of (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

There total 8 articles about (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 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: 80.0%

carbon disulfide (75-15-0,12122-00-8) + (5Z,7E)-(1S,3R,23R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10(19)-cholestatrien-23-ol (303015-23-8) + methyl iodide (74-88-4) → (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 (303015-24-9)

Guidance literature:

carbon disulfide; (5Z,7E)-(1S,3R,23R)-1,3-bis[(t-butyldimethylsilyl)oxy]-26,26,26,27,27,27-hexafluoro-25-methoxymethoxy-9,10-seco-5,7,10⁽¹⁹⁾-cholestatrien-23-ol; With 1H-imidazole; sodium hydride; In tetrahydrofuran; at 20 ℃;

methyl iodide; at 20 ℃; for 2h;

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)-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 (303015-24-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 91 percent / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

2.1: 92 percent / NMO; 4 Angstroem MS / tetrapropylammonium perrutenate / CH₂Cl₂ / 0.25 h / 20 °C

3.1: 82 percent / LiN(TMS)2 / tetrahydrofuran / 0.5 h / -70 °C

4.1: 52 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / -10 °C

5.1: 97 percent / pyridine / 12 h / 20 °C

6.1: 89 percent / iPr₂NEt / CHCl₃ / 1 h / Heating

7.1: 94 percent / 5 percent KOH / methanol / 1 h / 0 °C

8.1: NaH; imidazole / tetrahydrofuran / 20 °C

8.2: 80 percent / 2 h / 20 °C

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; 4 Angstroem MS; sodium hydride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; 1.1: Grignard reaction / 2.1: Oxidation / 3.1: Condensation / 4.1: Reduction / 5.1: Acetylation / 6.1: Alkylation / 7.1: Deacetylation / 8.1: thiocarbonylation / 8.2: Methylation;

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)-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 (303015-24-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 92 percent / NMO; 4 Angstroem MS / tetrapropylammonium perrutenate / CH₂Cl₂ / 0.25 h / 20 °C

2.1: 82 percent / LiN(TMS)2 / tetrahydrofuran / 0.5 h / -70 °C

3.1: 52 percent / NaBH₄ / tetrahydrofuran; methanol / 0.17 h / -10 °C

4.1: 97 percent / pyridine / 12 h / 20 °C

5.1: 89 percent / iPr₂NEt / CHCl₃ / 1 h / Heating

6.1: 94 percent / 5 percent KOH / methanol / 1 h / 0 °C

7.1: NaH; imidazole / tetrahydrofuran / 20 °C

7.2: 80 percent / 2 h / 20 °C

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; 4 Angstroem MS; sodium hydride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; 1.1: Oxidation / 2.1: Condensation / 3.1: Reduction / 4.1: Acetylation / 5.1: Alkylation / 6.1: Deacetylation / 7.1: thiocarbonylation / 7.2: Methylation;

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

upstream raw materials:

carbon disulfide

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

methyl iodide

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

Downstream raw materials:

(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

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

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