126092-07-7Relevant academic research and scientific papers
Facile construction of 1,2-cis glucosidic linkage using sequential oxidation-reduction route for synthesis of an ER processing α-glucosidase i substrate
Iino, Kenta,Iwamoto, Shogo,Kasahara, Yuta,Matsuda, Kana,Tonozuka, Takashi,Nishikawa, Atsushi,Ito, Yukishige,Matsuo, Ichiro
, p. 4452 - 4456 (2012)
The fluorescence-labeled hexasaccharide (Glcα1-2Glcα1- 3Glcα1-3Manα1-2Manα1-2Manα) was synthesized as a substrate for the processing enzyme α-glucosidase I. To construct the 1,2-cis glucosidic linkages, we employed an α stereoselective coupling using the mannosyl donor by assisted neighboring-group participation, followed by conversion of the stereochemistry of the C-2 hydroxyl group in the mannose residue using sequential oxidation of C-2 hydroxyl group to a 2-keto group and stereoselective reduction of the hydroxyl group to the gluco-configuration to provide the corresponding α-glucoside derivative. Using this strategy, the three consecutive α-glucosidic linkages were easily obtained in a stereoselective manner. Finally, the Dansyl labeled hexasaccharide derivative was used to measure the activity of processing α-glucosidase I.
Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents
Gomez, Ana M.,Casillas, Marta,Barrio, Aitor,Gawel, Anna,Lopez, J. Cristobal
experimental part, p. 3933 - 3942 (2009/04/08)
Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that und
