18026-23-8Relevant academic research and scientific papers
Enantioseparation on Riboflavin Derivatives Chemically Bonded to Silica Gel as Chiral Stationary Phases for HPLC
Kumano, Daisuke,Iwahana, Soichiro,Iida, Hiroki,Shen, Chengshuo,Crassous, Jeanne,Yashima, Eiji
supporting information, p. 507 - 517 (2015/08/03)
Acetylated and/or 3,5-dimethylphenylcarbamated riboflavins were prepared and the resulting riboflavin derivatives as well as natural riboflavin were regioselectively immobilized on silica gel through chemical bonding at the 5'-O- or 3-N-position of the riboflavin to develop novel chiral stationary phases (CSPs) for enantioseparation by high-performance liquid chromatography (HPLC). The chiral recognition abilities of the obtained CSPs were significantly dependent on the structures of the riboflavin derivatives, the position of the chemical bonding on the silica gel, and the structures of the racemic compounds. The CSPs bonded at the 5'-O-position on the silica gel tended to well separate helicene derivatives, while the CSPs bonded at the 3-N-position composed of acetylated and 3,5-dimethylphenylcarbamated riboflavins showed a better resolving ability toward helicene derivatives and bulky aromatic racemic alcohols, respectively, and some of them were completely separated into the enantiomers. The observed difference in the chiral recognition abilities of these riboflavin-based CSPs is discussed based on the difference in their structures, including the substituents of riboflavin and the positions immobilized on the silica gel. Chirality 27:507-517, 2015.
Filler for Optical Isomer Separation
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Page/Page column 9; 11, (2009/05/28)
A polymer compound derivative, obtained by modifying part of the hydroxy or amino groups of a polymer compound having the hydroxy or amino groups with molecules of a compound represented by the following general formula (I): A-X—Si(Y)nR3-n (I), where A represents a reactive group which reacts with a hydroxy or amino group, X represents an alkylene group which has 1 to 18 carbon atoms and which may have a branch, or an arylene group which may have a substituent, Y represents a reactive group which reacts with a silanol group to form a siloxane bond, R represents an alkyl group which has 1 to 18 carbon atoms and which may have a branch, or an aryl group which may have a substituent, and n represents an integer of 1 to 3.
Asymmetrie allylation of methyl ketones by using chiral phenyl carbinols
Tietze, Lutz F.,Kinzel, Tom,Wolfram, Thomas
experimental part, p. 6199 - 6210 (2010/03/01)
Novel chiral auxiliaries for the stereoselective allylation of aliphatic methyl ketones with allyltrimethylsilane and their use in the synthesis of homoallylic ethers are described. In a multicomponent domino process catalyzed by trifluoromethanesulfonic
SEPARATING AGENT FOR OPTICAL ISOMER AND METHOD FOR PREPARATION THEREOF
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Page/Page column 7-8, (2010/02/10)
To provide a separating agent which combines a high optical resolving power inherent in polysaccharide derivatives with sufficient solvent resistance and a method with which the separating agent can be produced efficiently in short steps. The separating agent for enantiomeric isomers is characterized in that a polymerizable polysaccharide derivative of a polysaccharide derivative having polymerizable functional groups and a polymerizable monomer having polymerizable unsaturated groups are copolymerized with a carrier having polymerizable functional groups to be chemically bound mutually. The separating agent is preferably used for high performance liquid chromatography (HPLC), and is excellent in solvent resistance.
HPLC enantioseparation with cellulose tris(3,5-dichlorophenylcarbamate) in aqueous methanol as a mobile phase
Chankvetadze, Bezhan,Yamamoto, Chiyo,Okamoto, Yoshio
, p. 352 - 353 (2007/10/03)
The appropriate design of mobile and stationary phase combinations allowed the use of cellulose tris(3,5-dichlorophenylcarbamate) (CDCPC) as the chiral stationary phase (CSP) in high-performance liquid chromatography (HPLC). Together with previous data obtained in n-hexane/2-propanol as a mobile phase the present study indicates very high chiral resolving ability of CDCPC.
Zinc-Promoted Reactions. 1. Mechanism of the Clemmensen Reaction. Reduction of Benzophenone in Glacial Acetic Acid
Vona, Maria Luisa Di,Rosnati, Vittorio
, p. 4269 - 4273 (2007/10/02)
The mechanism of the Clemmensen reduction of diaryl ketones was investigated by reducing benzophenone, benzhydryl chloride, and dichlorodiphenylmethane in AcOH under a variety of conditions.Besides diphenylmethane, dimeric products were isolated that were indicative of the formation of radical species.Different product distributions were obtained from reactions run under different conditions.The reduction of deuteriated benzhydryl chloride was also performed.A quite complicated mechanistic pattern, involving ionic and nonionic reactions, emerged from the experimental p icture.Two pathways, connected through the protonated substrate, were recognized.According to the first pathway the reduction is promoted by a SET from Zn to the substrate, leading to the formation of a carbon radical having one zinc atom bound to the oxygen of the carbonyl group.Benzhydryl chloride, benzhydryl acetate, and dichlorodiphenylmethane are involved in the process.The product distributions suggest the occurrence of several SETs, which involve the formation of different radical species.Ionic reactions are responsible for the second route to the reduced products.Nucleophilic displacements also participate to the complex mechanism.
