481-20-9

Usage

InChI:InChI=1/C27H48/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h19-25H,6-18H2,1-5H3/t20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 5211-17-6 β-Cholestanyl-S-methyl-xanthat 
• 130534-82-6 Thiocarbonic acid O-[(3S,5S,10S,13R,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester O-(4-fluoro-phenyl) ester 
• 27425-93-0 cholesta-4,6-diene 
• 16732-86-8 cholest-4-ene 
• 604-35-3 Cholesteryl acetate 
• 1255-88-5 5α-cholestan-3β-yl acetate 
• 4947-63-1 5α-cholestan-3β-yl acetate 
• 72536-56-2 3α-isothiocyanatocholestane 
• 17320-11-5 cholest-5-ene-3β,4β-diyl diacetate 
• 60-29-7 diethyl ether 
• 64-19-7 acetic acid 
• 141-78-6 ethyl acetate 
• 747-90-0 3,5-cholestadiene 
• 123-51-3 i-Amyl alcohol 

Downstream Products

• 25312-65-6 cholanic acid 
• 18089-10-6 6-Methoxycholestan 
• 99299-17-9 6-(Methoxymethoxy)cholestan 
• 963-74-6 5alpha-androstan-17-one 
• 63-05-8 Androstenedione 
• 57-88-5 cholesterol 
• 601-57-0 Cholest-4-en-3-one 

Relevant academic research and scientific papers

Hydropyrolysis over a platinum catalyst as a preparative technique for the compound-specific carbon isotope ratio measurement of C27 steroids

Compound-specific stable carbon isotope analysis by gas chromatography/combustion/isotope ratio mass spectrometry (GC/C/IRMS) is an important method for the determination of the 13C/12C ratios of biomolecules such as steroids, for a wide range of applications. However, steroids in their natural form exhibit poor chromatographic resolution, while derivatisation adds carbon thereby corrupting the stable isotopic composition. Hydropyrolysis with a sulphided molybdenum catalyst has been shown to defunctionalise the steroids, while leaving their carbon skeleton intact, allowing for the accurate measurement of carbon isotope ratios. The presence of double bonds in unsaturated steroids such as cholesterol resulted in significant rearrangement of the products, but replacing the original catalyst system with one of platinum results in higher conversions and far greater selectivity. The improved chromatographic performance of the products should allow GC/C/IRMS to be applied to more structurally complex steroid hormones and their metabolites.

Novel electrochemical deoxygenation reaction using diphenylphosphinates

The electrochemical reduction of diphenylphosphinate esters leads smoothly and in high yields to the corresponding deoxygenated products. In comparison with the previously developed methodologies, the electrolysis could be performed at lower temperature and with a higher current density, resulting in a shorter reaction time.

Action of lithium ethylenediamine on 1,4-diketone

Reactions of lithium ethylenediamine (Li/EDA) have been carried out on 1,4-diketones such as cholest-4(5)-en-3,6-dione (1) and hexane-2,5-dione (7). The resulting compounds have been characterized by optical rotation, IR, mass spectra and by comparison with authentic samples.

Using toluates as simple and versatile radical precursors

(Chemical Equation Presented) The viability of the toluate moiety as a radical precursor has been examined by studying deoxygenation and cyclization reactions.

Safe, facile radical-based reduction and hydrosilylation reactions in a microreactor using tris(trimethylsilyl)silane

A highly efficient system for tris(trimethylsilyl)silane (TTMSS) mediated deoxygenation, dehalogenation and hydrosilylation reactions is described in a microstructured device; this convenient platform enables the scale up of radical-based processes. The Royal Society of Chemistry.

Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents

The chemoselectivity of rigid cyclic α,β-unsaturated carbonyl group on the reducing agents was influenced by the ring size and steric factor. Cholesterol (cholest-5-en-3β-ol) and dehydroepiandrosterone (DHEA) were oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione. They were reduced with NaBH4, lithium tri-sec-butylborohydride (l-Selectride), LiAlH4, 9-borabicyclo[3.3.1]nonane (9-BBN), lithium triethylborohydride (Super-hydride), and BH3·(CH3)2S in various conditions, respectively. Reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by NaBH4 (4 equiv.) produced 4,6-cholestadien-3β-ol and 4,6-androstadiene-3β,17β-diol, respectively. Reduction by l-Selectride (12 equiv.) afforded 4,6-cholestadien-3α-ol and 4,6-androstadiene-3α,17β-diol, chemoselectively. Reaction with Super-hydride (12 equiv.) produced 4,6-cholestadien-3-one and 3-oxo-4,6-androstadien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by 9-BBN (14 equiv.) produced 1,4,6-cholestatrien-3α-ol, but 1,4,6-androstatriene-3,17-dione was not reacted with 9-BBN in the reaction conditions. Reaction of LiAlH4 (6 equiv.) formed 4,6-cholestadien-3β-ol and 3-oxo-1,4,6-androstatrien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by BH3·(CH3)2S (11 equiv.) gave cholestane as major compound and unlike reactivity of cholesterol, 1,4,6-androstatriene-3,17-dione by 8 equiv. of BH3·(CH3)2S formed 3-oxo-1,4,6-androstatrien-17β-ol. LiAlH4 and BH3·(CH3)2S showed relatively low chemoselectivity.

Radical deoxygenation of alcohols and intermolecular carbon-carbon bond formation with surfactant-type radical chain carriers in water

An efficient and mild method is developed for radical deoxygenation of alcohols and formation of carbon-carbon bonds in water without adding additives such as surfactants. The reaction was applied to synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides that are potent anti-HIV agents. The reaction afforded environmentally benign reaction conditions.

One-pot synthesis of recyclable palladium catalysts for hydrogenations and carbon-carbon coupling reactions

Palladium nanoparticles were generated from tetrakis(triphenylphophine) palladium in a mixture of tetra(ethylene glycol) and tetramethoxysilane (or titanium(IV) isopropoxide), then encapsulated in silica matrix (or titania matrix) by the treatment with water. The resulting heterogeneous material showed high catalytic activity in the hydrogenations of various alkene and alkynes and in the carbon-carbon cross-coupling reactions such as the Suzuki-Miyaura, the Sonogashira, the Heck-Mizoroki, and the Stille reactions.

On reduction of α,β-unstaurated ketones and the respective allylic alcohols, bearing a phenylsulfonyl or phenylsulfanyl group in the a position. Hydroxy group-controlled stereoselective reduction of 3α- And 3β-hydroxy-4-(phenylsulfonyl)cholest-4-ene

Reduction reactions of chplest-4-en-3-one derivatives bearing the phenylsulfonyl or phenylsulfanyl group at C-4 with various metal hydrides are studied. Lithium aluminohydride reduction of 4-(phenylsulfonyl)cholest-4-en-3β-ol 13a and 4-(phenylsulfonyl)cholest-4-en-3α-ol 15a occurs with saturation of the double bond and deoxygenation to give 4β-phenylsulfonyl-5β-cholestane 8 and 4α-phenylsulfonyl-5α-cholestane 7a, respectively. Reduction of 4-(phenylsulfonyl)cholest-4-en-3-one 2 with lithium aluminohydride yields compound 8. Reduction of compounds 2, 13a and 15a with other metal hydrides affords mixtures of diastereomeric products. Metal hydride reductions of 4-(phenylsulfanyl)cholest-4-en-3-one 1 affect the carbonyl group only. Catalytic hydrogenation of compound 2 gives a mixture of 5α- and 5β- dihydro derivatives. Mechanistic and stereochemical aspects of the reduction reactions are discussed. The Royal Society of Chemistry 2000.