864966-90-5Relevant academic research and scientific papers
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
Stereocontrolled formation of β-glucosides and related linkages in the absence of neighboring group participation: Influence of a trans-fused 2,3-O-carbonate group
Crich, David,Jayalath, Prasanna
, p. 7252 - 7259 (2007/10/03)
Phenyl 4,6-di-O-benzyl-2,3-O-carbonyl-β-D-glucothiopyranoside and the regiosiomeric phenyl 2,6-di-O-benzyl-3,4-O-carbonyl-β-D-glucothiopyranoside were prepared and studied as glucosyl donors at -60 °C in dichloromethane with preactivation by 1-benzenesulf
