(25R)-26-Hydroxy-cholest-4-en-3-one

Base Information

• Chemical Name: (25R)-26-Hydroxy-cholest-4-en-3-one
• CAS No.: 56792-59-7
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.645
• Mol file: 56792-59-7.mol

Synonyms:

Chemical Property of (25R)-26-Hydroxy-cholest-4-en-3-one

Chemical Property:

• Melting Point: 136-138°C
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(25R)-26-Hydroxy-cholest-4-en-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (25R)-26-Hydroxy-cholest-4-en-3-one is an oxygenated sterol which has many important biological activities. (25R)-26-Hydroxy-cholest-4-en-3-one has been used as a reactant for the synthesis of other sterols.

Technology Process of (25R)-26-Hydroxy-cholest-4-en-3-one

There total 19 articles about (25R)-26-Hydroxy-cholest-4-en-3-one 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:

6β-methoxy-3α,5-cyclo-5α-chol-23-en-22-ol (57984-04-0,71424-84-5,71424-85-6) → (25ξ)-26-hydroxycholest-4-en-3-one (19257-21-7,41530-25-0,56792-59-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 76 percent / propionic acid / xylene / 3 h / Heating

2: 100 percent / H₂ / PtO₂ / hexane / 30 h / 760 Torr

3: 6.7 g / LAH / diethyl ether / 0.5 h / Ambient temperature

4: 98 percent / imidazole / dimethylformamide / 1 h

5: 89 percent / 0.67 h / Heating

6: LAH / diethyl ether / 1 h

7: pyridinium chlorochromate (PCC) / CH₂Cl₂ / 6 h

8: HCl / diethyl ether / 0.75 h / 0 °C

9: TBAF / tetrahydrofuran / 22 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; propionic acid; pyridinium chlorochromate; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; xylene;

Reference yield:

ethyl (25ξ,22E)-6β-methoxy-3α,5-cyclo-5α-cholest-22-en-26-oate (137436-15-8) → (25ξ)-26-hydroxycholest-4-en-3-one (19257-21-7,41530-25-0,56792-59-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / H₂ / PtO₂ / hexane / 30 h / 760 Torr

2: 6.7 g / LAH / diethyl ether / 0.5 h / Ambient temperature

3: 98 percent / imidazole / dimethylformamide / 1 h

4: 89 percent / 0.67 h / Heating

5: LAH / diethyl ether / 1 h

6: pyridinium chlorochromate (PCC) / CH₂Cl₂ / 6 h

7: HCl / diethyl ether / 0.75 h / 0 °C

8: TBAF / tetrahydrofuran / 22 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; pyridinium chlorochromate; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(8S,9S,10R,13R,14S,17R)-17-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyl]-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (137435-82-6) → (25ξ)-26-hydroxycholest-4-en-3-one (19257-21-7,41530-25-0,56792-59-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 22h; Yield given; Ambient temperature;

upstream raw materials:

26-hydroxycholesterol

(8S,9S,10R,13R,14S,17R)-17-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyl]-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

Kryptogenin

(R)-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-methyl-heptan-1-ol

Downstream raw materials:

Cholest-4-en-3-one

C₃₆H₅₄O₃S₃

(25R)-7α,26-dihydroxycholest-4-en-3-one

Refernces

• 1、 Driscoll, Max D.,McLean, Kirsty J.,Levy, Colin,Mast, Natalia,Pikuleva, Irina A.,Lafite, Pierre,Rigby, Stephen E. J.,Leys, David,Munro, Andrew W.. "Structural and biochemical characterization of Mycobacterium tuberculosis CYP142: Evidence for multiple cholesterol 27-hydroxylase activities in a human pathogen". experimental part. p. 38270 - 38282. Retrieved 2011/10/13.
• 2、 Rabinowitz, Michael H.,Djerassi, Carl. "Biosynthetic studies of marine lipids. 39.1 19-norsterols: The course of c-19 methyl elimination". . p. 304 - 317. Retrieved 2007/10/02.