9,10-Secocholesta-5,7,10(19),16,23-pentaene-1,3,25-triol,(1a,3b,5Z,7E,23E)- (9CI)

Base Information

• Chemical Name: 9,10-Secocholesta-5,7,10(19),16,23-pentaene-1,3,25-triol,(1a,3b,5Z,7E,23E)- (9CI)
• CAS No.: 124409-57-0
• Molecular Formula: C27H40 O3
• Molecular Weight: 412.613
• Mol file: 124409-57-0.mol

Synonyms:Ro24-2201

Chemical Property of 9,10-Secocholesta-5,7,10(19),16,23-pentaene-1,3,25-triol,(1a,3b,5Z,7E,23E)- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9,10-Secocholesta-5,7,10(19),16,23-pentaene-1,3,25-triol,(1a,3b,5Z,7E,23E)- (9CI)

There total 11 articles about 9,10-Secocholesta-5,7,10(19),16,23-pentaene-1,3,25-triol,(1a,3b,5Z,7E,23E)- (9CI) 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:

<3aR-(1Z,3aα,4β,7aβ)>-1-ethylideneoctahydro-7a-methyl-1H-inden-4-ol acetate (88803-21-8) → 1,25-dihydroxy-16,23E-diene-cholecalciferol (124409-57-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / dimethylaluminum chloride / CH₂Cl₂ / 3 h / -78 °C

2: 92 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

3: 88 percent / tri-n-butyltin hydride, AIBN / toluene / 0.25 h / 120 °C

4: 1.) tetrabutylammonium fluoride, 2.) potassium hydroxide / 1.) THF, room temperature, 2.) ethanol, water, 80 deg C, 3 h

5: 78 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 4 h / Ambient temperature

6: 99 percent / CH₂Cl₂ / 17 h / Ambient temperature

7: 92 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 45 °C

8: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

9: 1.) selenium dioxide, t-butyl hydroperoxide, 2.) Super-Hydride / 1.) dichloromethane, isooctane, 4 deg C, 48 h, 2.) THF, -60 deg C, 15 min

10: 72 percent / LiAlH₄ / tetrahydrofuran / 16 h / 65 °C

11: 1.) pyridinium p-toluenesulfonate, 2.) 9-acetoxyanthracene / 1.) acetonitrile, water, 65 deg C, 3 h, 2.) t-BuOMe, irradiation, 30 min

With pyridine; tert.-butylhydroperoxide; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; selenium(IV) oxide; 2,2'-azobis(isobutyronitrile); 9-acetoxyanthracene; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium acetate; dimethylaluminum chloride; pyridinium p-toluenesulfonate; lithium triethylborohydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1016/S0968-0896(98)00164-3

Reference yield:

4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-2-pentynal (157522-92-4) → 1,25-dihydroxy-16,23E-diene-cholecalciferol (124409-57-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / dimethylaluminum chloride / CH₂Cl₂ / 3 h / -78 °C

2: 92 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

3: 88 percent / tri-n-butyltin hydride, AIBN / toluene / 0.25 h / 120 °C

4: 1.) tetrabutylammonium fluoride, 2.) potassium hydroxide / 1.) THF, room temperature, 2.) ethanol, water, 80 deg C, 3 h

5: 78 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 4 h / Ambient temperature

6: 99 percent / CH₂Cl₂ / 17 h / Ambient temperature

7: 92 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 45 °C

8: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

9: 1.) selenium dioxide, t-butyl hydroperoxide, 2.) Super-Hydride / 1.) dichloromethane, isooctane, 4 deg C, 48 h, 2.) THF, -60 deg C, 15 min

10: 72 percent / LiAlH₄ / tetrahydrofuran / 16 h / 65 °C

11: 1.) pyridinium p-toluenesulfonate, 2.) 9-acetoxyanthracene / 1.) acetonitrile, water, 65 deg C, 3 h, 2.) t-BuOMe, irradiation, 30 min

With pyridine; tert.-butylhydroperoxide; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; selenium(IV) oxide; 2,2'-azobis(isobutyronitrile); 9-acetoxyanthracene; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium acetate; dimethylaluminum chloride; pyridinium p-toluenesulfonate; lithium triethylborohydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1016/S0968-0896(98)00164-3

Reference yield:

<3aR-<1(R*),3aα,7aβ>>-3,3a,5,6,7,7a-hexahydro-1-(5-hydroxy-1,5-dimethyl-3-hexynyl)-7a-methyl-1H-inden-4-one (124409-70-7) → 1,25-dihydroxy-16,23E-diene-cholecalciferol (124409-57-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / CH₂Cl₂ / 17 h / Ambient temperature

2: 92 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 45 °C

3: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) selenium dioxide, t-butyl hydroperoxide, 2.) Super-Hydride / 1.) dichloromethane, isooctane, 4 deg C, 48 h, 2.) THF, -60 deg C, 15 min

5: 72 percent / LiAlH₄ / tetrahydrofuran / 16 h / 65 °C

6: 1.) pyridinium p-toluenesulfonate, 2.) 9-acetoxyanthracene / 1.) acetonitrile, water, 65 deg C, 3 h, 2.) t-BuOMe, irradiation, 30 min

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; selenium(IV) oxide; 9-acetoxyanthracene; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; lithium triethylborohydride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0968-0896(98)00164-3

upstream raw materials:

(1α,3α,5α,6E,23E)-3,5-cyclo-9,10-secocholesta-6,10(19),16,23-tetraene-1,8,25-triol

<3aR-(1Z,3aα,4β,7aβ)>-1-ethylideneoctahydro-7a-methyl-1H-inden-4-ol acetate

4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-2-pentynal

<3aR-<1(R*),3aα,7aβ>>-3,3a,5,6,7,7a-hexahydro-1-(5-hydroxy-1,5-dimethyl-3-hexynyl)-7a-methyl-1H-inden-4-one

Refernces