Synthesis of N-glycosides. An alternative approach based on diastereoselective base coupling and S(N)2 cyclization.
[reaction: see text] Acyclic diastereoselection is achieved for the formation of thioaminyl acetals. The highly intramolecular stereocontrolled S(N)2 displacement of the thioaminyls allows for the formation of cyclic nucleoside derivatives. This versatile approach may provide easy access to a large variety of N-glycosides.
Guindon
Yvan
Y
Institut de recherches cliniques de Montréal (IRCM), Bio-organic Chemistry Laboratory, 110 avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7. guindoy@ircm.qc.ca
Gagnon
Marc
M
Thumin
Isabelle
I
Chapdelaine
Daniel
D
Jung
Grace
G
Guérin
Brigitte
B
D000606:Amino Sugars / Q000138:chemical synthesis; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis*; D009705:Nucleosides / Q000138:chemical synthesis; D013237:Stereoisomerism
D000606:Amino Sugars; D006027:Glycosides; D009705:Nucleosides