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

Base Information

Chemical Name:(6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol
CAS No.:210907-40-7
Molecular Formula:C₂₇H₃₈F₆O₃
Molecular Weight:524.587
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol

There total 12 articles about (6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol 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: 66.0%

: 210907-37-2
(6Z)-(3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5⁽¹⁰⁾,6,8-cholestatriene-3,25-diol-1-one

: 210907-40-7
(6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 1.5h;
DOI:10.1016/S0968-0896(00)00142-5

Reference yield:

: 143884-26-8
(5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene

: 210907-40-7
(6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol

Guidance literature:: Multi-step reaction with 12 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

9.1: 97 percent / nBu₃SnH / toluene / 1 h / Heating

10.1: 56 percent / MsOH / methanol / 2 h / 20 °C

11.1: 66 percent / Dess-Martin periodinane / acetonitrile / 4 h / 20 °C

12.1: 66 percent / NaBH₄ / methanol / 1.5 h / 0 °C

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; methanesulfonic acid; 4 Angstroem MS; tri-n-butyl-tin hydride; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; toluene; acetonitrile; 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 / 9.1: Reduction / 10.1: Hydrolysis / 11.1: Oxidation / 12.1: Reduction;
DOI:10.1016/S0968-0896(00)00142-5

Reference yield:

: 167892-98-0
(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

: 210907-40-7
(6Z)-(1R,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5(10),6,8-cholestatriene-1β,3β,25-triol

Guidance literature:: Multi-step reaction with 11 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

8.1: 97 percent / nBu₃SnH / toluene / 1 h / Heating

9.1: 56 percent / MsOH / methanol / 2 h / 20 °C

10.1: 66 percent / Dess-Martin periodinane / acetonitrile / 4 h / 20 °C

11.1: 66 percent / NaBH₄ / methanol / 1.5 h / 0 °C

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; methanesulfonic acid; 4 Angstroem MS; tri-n-butyl-tin hydride; sodium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; toluene; acetonitrile; 1.1: Oxidation / 2.1: Condensation / 3.1: Reduction / 4.1: Acetylation / 5.1: Alkylation / 6.1: Deacetylation / 7.1: thiocarbonylation / 7.2: Methylation / 8.1: Reduction / 9.1: Hydrolysis / 10.1: Oxidation / 11.1: Reduction;
DOI:10.1016/S0968-0896(00)00142-5