1456718-89-0Relevant academic research and scientific papers
Reagent Controlled Stereoselective Synthesis of α-Glucans
Wang, Liming,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Codée, Jeroen D. C.
supporting information, p. 4632 - 4638 (2018/04/10)
The development of a general glycosylation method that allows for the stereoselective construction of glycosidic linkages is a tremendous challenge. Because of the differences in steric and electronic properties of the building blocks used, the outcome of
Rapid Synthesis of l-Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides
Herczeg, Mihály,Demeter, Fruzsina,Balogh, Tímea,Kelemen, Viktor,Borbás, Anikó
supporting information, p. 3312 - 3316 (2018/07/13)
A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l-idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6-acetal formation. The α-anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l-ido diastereoselectivity. The 4,6-arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α-idosylation could be achieved by using idosyl donors without a C-2 participating group.
Synthesis of 6-sulfonatomethyl thioglycosides by nucleophilic substitution: Methods to prevent 1→6 anomeric group migration of thioglycoside 6-o-triflates
Herczeg, Mihaly,Mezo, Erika,Eszenyi, Daniel,Lazar, Laszlo,Csavas, Magdolna,Bereczki, Ilona,Antus, Sandor,Borbas, Aniko
supporting information, p. 5570 - 5573 (2013/09/12)
Introduction of a sulfonatomethyl moiety into the primary position of thioglycosides by nucleophilic displacement of the corresponding 6-O-triflate is described. The 1→6 migration of the anomeric group, which inevitably occurs through a bicyclic sulfonium ion intermediate, from conformationally flexible β-thioglycosides was prevented by using an α-thioglycoside or conformationally locked β-thioglycoside as the starting material. The thioglycoside 6-sulfonic acids showed excellent α-selectivity during synthesis of uronic acid containing heparinoid trisaccharides. Two routes to prepare C6-sulfonatomethyl thioglucosides by displacement of a 6-O-triflate moiety are reported. The undesired participation of the β-thio aglycon is prevented by changing the anomeric configuration or by locking the pyranose ring. The 6-sulfonatomethyl donors show excellent α-selectivities but significantly different reactivities during the synthesis of heparinoid trisaccharides. Copyright
