3381-52-0Relevant academic research and scientific papers
A mild and efficient oxidation of primary alkyl iodides to carboxylic acids
Hernandez,Melian,Suarez
, p. 653 - 655 (1992)
A one-step method for the preparation of carboxylic acids from primary alkyl iodides by treatment with ruthenium tetroxide is described.
Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles
Alexanian, Erik J.,Tercenio, Quentin D.
supporting information, p. 7215 - 7219 (2021/09/22)
The stereospecific cross-coupling of easily accessed electrophiles holds significant promise in the construction of C-C bonds. Herein, we report a nickel-catalyzed reductive coupling of allyl alcohols with chiral, nonracemic alkyl tosylates. This cross-coupling delivers valuable allylation products with high levels of stereospecificity across a range of substrates. The catalytic system consists of a simple nickel salt in conjunction with a commercially available reductant and importantly represents a rare example of a cross-coupling involving the C-O bonds of two electrophiles.
Site-Selective Thiolation of (Multi)halogenated Heteroarenes
Sandfort, Frederik,Knecht, Tobias,Pinkert, Tobias,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 6913 - 6919 (2020/05/14)
A general and simple strategy for the site-selective thiolation of various pharmaceutically relevant electron-rich heteroarenes with thiols is reported. This mild and reliable photocatalytic protocol enables C-S coupling at the most electron-rich position of the (multi)halogenated substrates, complementing established methodologies. Experimental and computational studies suggest a radical chain mechanism with the key step being a homolytic aromatic substitution of the heteroaryl halide by an electrophilic thiyl radical, highlighting an underdeveloped reactivity mode.
Novel steroid -based amphiphiles and uses thereof
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Paragraph 0208-0211, (2020/05/23)
The present invention relates to a newly developed steroid-based amphiphilic compound, a preparation method thereof and a method for extracting, solubilizing, stabilizing, crystallizing or analyzing membrane proteins using the same. In addition, the compound, compared to the conventional compounds, can efficiently extract membrane proteins having various structures and properties from cell membranes and store the same in an aqueous solution for a long time, and thus can be used for functional analysis and structural analysis. Membrane protein structure and function analysis thereof is one of the areas of greatest interest in current biology and chemistry by being closely related to drug development.COPYRIGHT KIPO 2020
Modification in the side chain of solomonsterol A: Discovery of cholestan disulfate as a potent pregnane-X-receptor agonist
Sepe, Valentina,Ummarino, Raffaella,D'Auria, Maria Valeria,Lauro, Gianluigi,Bifulco, Giuseppe,D'Amore, Claudio,Renga, Barbara,Fiorucci, Stefano,Zampella, Angela
, p. 6350 - 6362 (2012/09/05)
Seven synthetic analogues of the PXR (pregnane-X-receptor) potent natural agonist solomonsterol A were prepared by total synthesis. Their activity toward PXR was assessed by transactivation and RT-PCR assays. The study discloses cholestan disulfate (8) as a new, simplified agonist of PXR. By in vitro studies on hepatic cells we have demonstrated that this compound is a potent PXR agonist and functional characterization in human macrophages and hepatic stellate cells provided evidence that cholestan disulfate (8) has the ability to modulate the immune response triggered by bacterial endotoxin as well as to counter-activate hepatic stellate cell activation induced by thrombin. Because inhibition of immune-driven circuits might have relevance in the treatment of inflammation and liver fibrosis, the present data support the development of cholestan disulfate (8) in preclinical models of inflammatory diseases. The Royal Society of Chemistry 2012.
Clarification of the stereochemical course of nucleophilic substitution of arylsulfonate-based nucleophile assisting leaving groups
Braddock, D. Christopher,Pouwer, Rebecca H.,Burton, Jonathan W.,Broadwith, Phillip
supporting information; experimental part, p. 6042 - 6049 (2009/12/24)
(Chemical Equation Presented) Secondary alcohols modified as tosylates, PEG-sulfonates, or quisylates undergo inversion of configuration at the reacting center when treated with lithium halide in acetone at reflux, where the PEG-sulfonates and quisylates are substantially more reactive. In sterically hindered cases, elimination is a competing process. In contrast, when treated with TiCl4, simple secondary sulfonates give chloride products with partial inversion of configuration. Any observed retention of configuration in a given alkyl sulfonate substrate under these conditions is likely due to neighboring group participation or diastereoselective attack on a carbocation (or ion pair) rather than an SNi mechanism.
Atypical regioselective biohydrolysis on steroidal oxiranes by Aspergillus niger whole cells: Some stereochemical features
Bisogno, Fabricio R.,Orden, Alejandro A.,Pranzoni, Celeste Aguirre,Cifuente, Diego A.,Giordano, Oscar S.,Kurina Sanz, Marcela
, p. 643 - 652 (2008/02/04)
5,6-Epoxycholestan-3β-ol derivatives were hydrolyzed in a diastereoconvergent manner by growing and resting cells of several strains of Aspergillus niger, particularly A. niger ATCC 11394. These strains displayed opposite regioselectivity toward each isomer in an α and β epoxide mixture, thus, the nucleophilic attack took place at the less substituted and the most substituted carbon atom on each diasteromer, respectively. These biocatalysts opened trisubstituted oxiranes but were unable to hydrolyze the disubstituted oxiranes in the tested sterol derivatives. These findings suggest that A. niger strains possess another hydrolytic ability different from the commercial A. niger epoxide hydrolase (EH) that did not accept this kind of steroidal oxiranes as substrates.
Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
Garrido Santos, Gustavo A.,Murray, Ana P.,Pujol, Carlos A.,Damonte, Elsa B.,Maier, Marta S.
, p. 125 - 132 (2007/10/03)
Five new steroid sulfates, sodium 2β,3α-dihydroxy-5α-cholestane 3-sulfate (6), sodium 2β,3α-dihydroxy-5α-cholestane 2-sulfate (7), disodium 2β,3α-dihydroxy-5α-cholestane disulfate (8), sodium 3α-acetoxy-2β-hydroxy-5α-cholestane 2-sulfate (12), and sodium
An efficient rearrangement of secondary alkyl S-methyl xanthates by trimethylaluminum (TMA)
Barton, Derek H. R.,Choi, Seung-Yong
, p. 2695 - 2698 (2007/10/03)
The rearrangement of secondary S-methyl xanthates to S-methyl dithiocarbonates at room temperature using trimethylaluminum has been studied. This reaction affords an efficient and simple method for converting secondary alcohols to thiols.
Syntheses and CD Studies of 5α-Cholesteno-, -- and -pyrimidines
Hasan, Mashooda,Rashid, Naghmana,Khan, Khalid Mohammed,Snatzke, Guenther,Duddeck, Helmut,Voelter, Wolfgang
, p. 889 - 896 (2007/10/02)
Syntheses of 5α-cholesteno- (5a), - (12a), and pyrimidines (15a) have been achieved by using hydroxymethylene derivatives of relevant cholestanones prepared from cholesterol (1).Their CD spectra exhibit at least three Cotton effects between 300 to 200 nm, a first CD band around 290, a second one around 260 and a third one around 220 nm.A quadrant rule is developed and applied to the determination of the first CD band, while a helicity rule is applicable to the third CD band.The first band is positive in the series, whereas it is negative in the and the series.The third band is negative in all three series. - Key Words: Cholestenopyrimidines / Circular dichroism / Quadrant rule of cholestenopyrimidines
