944733-25-9Relevant academic research and scientific papers
Addition of difluoromethyl radicals to glycals: A new route to α-CF2-D-glycosides
Moreno, Benjamin,Quehen, Cindy,Rose-Helene, Maureen,Leclerc, Eric,Quirion, Jean-Charles
, p. 2477 - 2480 (2007)
The synthesis of synthetically useful α-CF2 glycosides by radical addition of ethyl bromodifluoroacetate onto 2-benzyloxyglycals Is described. The methodology provides an access to α-O-glycoside mimics and, potentially, to valuable α-O-glycocon
Addition of electrophilic radicals to 2-benzyloxyglycals: Synthesis and functionalization of fluorinated α-C-glycosides and derivatives
Colombel, Sophie,Vana Hijfte, Nathalie,Poisson, Thomas,Leclerc, Eric,Pannecoucke, Xavier
, p. 12778 - 12787 (2013/10/01)
A new method for the synthesis of fluorinated α-C-glycosides is described. The reactions between highly electrophilic radicals (fluorinated or unfluorinated) and a 2-benzyloxyglucal or galactal provide 2-keto-D-arabino- or 2-keto-D-lyxo-hexopyranosides th
Straightforward preparation of functionalized α-CF 2-galactosides through an oxygen to carbon acyl migration
Colombel, Sophie,Sanselme, Morgane,Leclerc, Eric,Quirion, Jean-Charles,Pannecoucke, Xavier
supporting information; experimental part, p. 5238 - 5241 (2011/07/07)
A privileged Glycon! A radical-addition Meerwein-Ponndorf-Verley (MPV) reduction sequence provides access to functionalized α-CF 2-galactosides (see scheme). Introduction of a CF2Br group in the pseudo-anomeric position aided the transfer of an aglycon chain from O-2 to C-1′ through an intramolecular addition-reduction sequence, which involved a Br-Li exchange. This methodology gives access to a wide range of fluorinated C-glycosidic analogues of glycoconjugates.
