112289-38-0Relevant articles and documents
A simple and highly diastereoselective preparation of glycal epoxides using the MCPBA-KF complex
Bellucci, Giuseppe,Catelani, Giorgio,Chiappe, Cinzia,D'Andrea, Felicia
, p. 8433 - 8436 (1994)
Glycals are converted ro the corresponding epoxides in high yields by a diastereoselective one-step epoxidation using the m-chloroperoxybenzoic acid-KF complex in anhydrous dichloromethane.
C-glycosides: A stereoselective synthesis of α- and β-C-galactosides with glycosyl dianions
Burkhart, Fred,Hoffmann, Matthias,Kessler, Horst
, p. 7699 - 7702 (1998)
α- or β-C-galactosides can be obtained from the configurationally stable anomeric glycosyl dianions which are prepared by transmetallation of a tin compound or by reductive lithiation of a chloride. Different electrophiles react selectively at the anomeric center.
A short route to nucleoside diphosphate activated D- and L-hexoses
Ernst, Christiane,Klaffke, Werner
, p. 2973 - 2975 (2001)
Leloir transferases utilise nucleoside diphosphate sugars, which are notoriously difficult to synthesise and handle. Starting off from D- or L-configurated glycals, a facile synthesis of nucleotide sugars by epoxidation and direct coupling with uridine di
α-C-Glycosides via syn Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/n-Dibutyl Ether
Wagschal, Simon,Guilbaud, Johan,Rabet, Pauline,Farina, Vittorio,Lemaire, Sébastien
, p. 9328 - 9335 (2015)
The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 °C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different O-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the α-anomer of canagliflozin.
Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides
Santiago, Cintia C.,Lafuente, Leticia,Bravo, Rodolfo,Díaz, Gisela,Ponzinibbio, Agustín
, p. 3739 - 3742 (2017/09/02)
Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL's as catalysts. β-O