Cover Feature: Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses and Methyl Furanosyl Uronates (Chem. Eur. J. 29/2019)

• Published in: Chemistry : a European journal Vol. 25; no. 29; p. 7042
• Main Authors: 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.
• Format: Journal Article
• Language: English
• Published: 23-05-2019
• Subjects: conformation analysis; energy landscape maps; glycosylation; oxocarbenium ions; substituent effect
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201901260

Energy maps of the full conformational space of 5‐membered ring glycosyl oxocarbenium ions have been generated to probe the stereoelectronic effects of C‐2‐fluoride, C‐2‐azide and C‐4‐carboxylic acid ester substituents. The computational results describing the overall shape of the reactive intermediates were complemented by experiments to show that the vast majority of studied furanosides react in an 1,2‐cis selective manner in SN1‐type glycosylation reactions. More information can be found in the Full Paper by J. D. C. Codée et al. on page 7149.