28338-69-4

Basic information

• Product Name: 5α-Cholest-3-ene
• Synonyms: 5α-Cholest-3-ene
• CAS NO: 28338-69-4
• Molecular Formula: C₂₇H₄₆
• Molecular Weight: 370.65414
• Mol File: 28338-69-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5α-Cholest-3-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 5α-Cholest-3-ene(28338-69-4)
• EPA Substance Registry System: 5α-Cholest-3-ene(28338-69-4)

Safety Data

• Hazardous Substances Data: 28338-69-4(Hazardous Substances Data)

Upstream product

• 7755-25-1 5α-cholestanyl 4α-acetate 
• 3381-53-1 3α-cholestanyl mesylate 
• 17265-04-2 cesium benzoate 
• 958883-17-5 3-α-cholestanol 2-(prenyloxymethyl)benzoate 
• 3381-51-9 (3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl methanesulfonate 
• 102582-57-0 5α-cholestan-3β-yl trans-cinnamate 
• 182243-57-8 Chloro-methanesulfonic acid (3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 154592-73-1 N-(2,6-dimethylphenyl)selenocarbamate of cholestanol 
• 154592-71-9 N-(4-chlorophenyl)selenocarbamate of cholestanol 
• 154592-72-0 N-(4-fluorophenyl)selenocarbamate of cholestanol 
• 154592-69-5 N-cyclohexylselenocarbamate of cholestanol 
• 154592-70-8 N-phenylselenocarbamate of cholestanol 
• 138814-68-3 Formic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 67-56-1 methanol 

Downstream Products

• 481-21-0 cholestane 
• 1249-56-5 3α,4α-Epoxy-5α-cholestane 

Relevant articles and documents

2-(Prenyloxymethyl)benzoyl (POMB) group: a new temporary protecting group removable by intramolecular cyclization

2-(Prenyloxymethyl)benzoates can be prepared from alcohols and readily available 2-(prenyloxymethyl)benzoic acid by standard acylation techniques or by Mitsunobu reaction with inversion of configuration. The POMB group can be cleaved first by oxidative removal of the prenyl group with DDQ followed by lactonization with expulsion of the alcohol catalyzed by Yb(OTf)3. These reaction conditions are compatible with the presence of a large number of common protecting groups.

Chloromethanesulfonate as an efficient leaving group: Rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles

The chloromethanesulfonate (monochlate) served as an efficient leaving group for rearrangement of the carbon-carbon bond and conversion of alcohols into azides and nitriles. The treatment of the monochlate 16a with zinc acetate in dioxane at 90 °C effected migration of the 4α-methyl group to give alkene 17a. Upon similar treatment of the monochlates 22a, 25a, 28a, and 31a with zinc acetate, the carbon-carbon bonds antiperiplanar to the hydroxyl groups efficiently migrated to afford the alkenes 23a, 26a-c, 29a,b, and 32a, respectively. In the case of the diol 40, the monochlate was converted into the ketone 41 via a rearrangement-ring expansion. The reaction of the monochlates 44a, 47a, 49a, 52a, and 57a with sodium azide or lithium azide in N,N-dimethylformamide efficiently afforded the azides with inversion of the configuration. The introduction of a nitrile group to the sterically hindered alcohol 59 was performed in high yield by the reaction of the monochlate 60a with sodium cyanide.

Stereocontrolled formation of cis and trans ring junctions in hydrindane, decalin, and steroid systems by palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates

Both the cis and trans ring junctions can be generated selectively in hydrindane, decalin and steroid systems by the palladium-catalyzed regioselective and stereospecific decarboxylation-hydrogenolysis of allylic formates. The trans junctions were formed from 3β allylic formates of decalin and steroid and 5β allylic formates of hydrindane. The corresponding 3α and 5α formates generate the cis ring junction.