56376-32-0

Usage

Uses

Used in Pharmaceutical Industry:
(3beta,5alpha,6beta)-6-bromo-5-hydroxycholestan-3-yl acetate is used as a precursor for the synthesis of other biologically active molecules, given its unique structural features. Its potential role in creating new pharmaceutical compounds makes it a valuable asset in drug development.
Used in Chemical Research:
(3beta,5alpha,6beta)-6-bromo-5-hydroxycholestan-3-yl acetate serves as a research tool for studying the structure and function of cholesterol derivatives. Its distinct configuration allows scientists to explore the effects of structural variations on the properties and interactions of these molecules.
Further investigation through experimental studies is necessary to fully understand the specific properties and potential uses of (3beta,5alpha,6beta)-6-bromo-5-hydroxycholestan-3-yl acetate in various applications.

Upstream product

• 1256-31-1 Acetic acid (3S,5R,6S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-3-yl ester 
• 604-35-3 Cholesteryl acetate 
• 57-88-5 cholesterol 
• 1250-95-9 5α,6α-epoxycholestan-3β-ol 

Downstream Products

• 1250-95-9 5α,6α-epoxycholestan-3β-ol 
• 604-35-3 Cholesteryl acetate 

Relevant academic research and scientific papers

Bismuth(III) salts mediated regioselective ring opening of epoxides: an easy route to halohydrins and β-hydroxy nitrates

The ring opening of various epoxides was achieved under mild conditions using bismuth(III) salts. Halohydrins and β-hydroxy nitrates were efficiently obtained from the corresponding 5α,6α-, 2α,3α-, and 5β,6β-epoxysteroid using BiCl3, BiBr3

Sterol synthesis. Preparation and characterization of fluorinated and deuterated analogs of oxygenated derivatives of cholesterol

Oxygenated sterols, including both autoxidation products and sterol metabolites, have many important biological activities. Identification and quantitation of oxysterols by chromatographic and spectroscopic methods is greatly facilitated by the availability of authentic standards, and deuterated and fluorinated analogs are valuable as internal standards for quantitation. We describe the preparation, purification and characterization of 43 oxygenated sterols, including the 4β-hydroxy, 7α-hydroxy, 7β-hydroxy, 7-keto, and 19-hydroxy derivatives of cholesterol and their analogs with 25,26,26,26,27,27,27-heptafluoro (F7) and 26,26,26,27,27,27-hexadeuterio (d6) substitution. The 7α-hydroxy, 7β-hydroxy, and 7-keto derivatives of (25R)-cholest-5-ene-3β,26-diol (1d) and their 16,16-dideuterio analogs were also prepared. These d2-26-hydroxysterols and [16,16-2H2]-(25R)-cholest-5-ene-3β,26-diol (1e) were synthesized from [16,16-2H2]-(25R)-cholest-5-ene-3β,26-diol diacetate (2e), which can be prepared from diosgenin. The highly specific deuterium incorporation at C-16 in 1e and 2e should be useful in mass spectral analysis of 26-hydroxycholesterol samples by isotope dilution methods. The Δ5-3β,7α,26- and Δ5-3β,7β,26-triols were regioselectively oxidized/isomerized to the corresponding Δ4-3-ketosteroids with cholesterol oxidase. Also described are 5,6α-epoxy-5α-cholestan-3β-ol, its 5β,6β-isomer, cholestane-3β,5α,6β-triol, their F7 and d6 derivatives, and d3-25-hydroxycholesterol, which was prepared from 3β-acetoxy-27-norcholest-5-en-25-one (30). The 43 oxysterols and most synthetic intermediates were isolated in high purity and characterized by chromatographic and spectroscopic methods, including mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. Detailed mass spectral assignments are presented, and 1H NMR stereochemical assignments are derived for the C-19 protons of 19-hydroxysterols and for the side chain protons of 30. Copyright (C) 1999 Elsevier Science Ireland Ltd.

The Mechanism of the β-Acyloxyalkyl Radical Rearrangement: Kinetic and 18O-Labelling Studies

Experiments with 18O-enriched substrates indicate that the rearrangement of 2-butanoyloxy-2,2-dimethyl radical 1 (R=Pr) by migration of the acyloxy group involves complete transposition of the ether and carbonyl oxygen atoms, whereas the similar but much faster rearrangement of the substituted cholestanyl radical 11 proceeds with only 24percent transposition.The rearrangement of 1 is considered to involve a five-membered cyclic transition state 2, while that of 11 probably proceeds via a tight anion-radical-cation pair 21.

Use of Polymeric Phosphine-Halogen Complexes in the Conversion of Epoxides to Halohydrins

Polystyryldiphenylphosphine-halogen complexes are convenient reagents for converting epoxides to halohydrins under mild and non-acidic conditions.The method requires only a filtration and evaporation process for product isolation.

ON THE CONVERSION OF SUBSTITUTED EPOXIDES TO HALOHYDRINS

Di- and trisubstituted steroidal epoxides are shown to be converted smoothly to halohydrins in high yield by triphenylphosphine-halogen complexes, under non-acidic and non-eliminating conditions.