97949-53-6Relevant articles and documents
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.
Synthesis and immobilization of amylose derivatives bearing a 4-terf-butylbenzoate group at the 2-position and 3,5-dichlorophenylcarbamate/3- (triethoxysilyl)propylcarbamate groups at 3- And 6-positions as chiral packing material for HPLC
Shen, Jun,Ikai, Tomoyuki,Shen, Xiande,Okamoto, Yoshio
scheme or table, p. 442 - 444 (2010/09/05)
Two novel amylose derivatives 2a and 2b bearing A-tertbutylbenzoate at the 2-position and 3,5-dichlorophenylcarbamate/3-(triethoxysilyl)propylcarbamate residues at 3- and 6positions were successfully synthesized and immobilized onto silica gel, and their chiral recognition abilities were evaluated as chiral packing materials (CPMs) for high-performance liquid chromatography. These immobilized CPMs exhibited recognition ability similar to conventional coated CPM, and for some racemates, comparable or better resolutions were observed even compared to commercial immobilized amylose- or cellulosebased columns.
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