110237-88-2Relevant articles and documents
Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2-Azidofuranoses, 2-Fluorofuranoses and Methyl Furanosyl Uronates
van der Vorm, Stefan,Hansen, Thomas,van Rijssel, Erwin R.,Dekkers, Rolf,Madern, Jerre M.,Overkleeft, Herman S.,Filippov, Dmitri V.,van der Marel, Gijsbert A.,Codée, Jeroen D. C.
, (2019/04/30)
The 3D shape of glycosyl oxocarbenium ions determines their stability and reactivity and the stereochemical course of SN1 reactions taking place on these reactive intermediates is dictated by the conformation of these species. The nature and co
Synthesis of erythro and threo furanoid glycals using 5-endo-trig selenoetherification as key step
Bravo,Kassou,Castillon
, p. 1187 - 1190 (2007/10/03)
Differently protected erythro and threo furanoid glycals were synthesised from 4-pentene-1,2,3-triol, through selenium induced 5-endo-trig cyclization and selenoxide elimination.
An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols
Robles, Rafael,Rodriguez, Concepcion,Izquierdo, Isidoro,Plaza, Maria T.,Mota, Antonio
, p. 2959 - 2965 (2007/10/03)
Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-β-D-xylo-pentofuranosyl 5-10 and β-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed.