Stereoselective Construction of Orthogonally Protected, N–O Interlinked Disaccharide Mimetics Using N‑Substituted β‑Aminooxy Donors

Orthogonally protected N-substituted β-aminooxy sugars can be stereoselectively synthesized from sugar epoxides and nitrones derived from aromatic aldehydes. Both the ether- and ester-protected sugar epoxides can be employed. The synthesized aminooxy sugars could be reacted with aldehyde bearing/fre...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2022-04, Vol.87 (8), p.5125-5135
Hauptverfasser: Ahmed, Ajaz, Mukherjee, Debaraj
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Orthogonally protected N-substituted β-aminooxy sugars can be stereoselectively synthesized from sugar epoxides and nitrones derived from aromatic aldehydes. Both the ether- and ester-protected sugar epoxides can be employed. The synthesized aminooxy sugars could be reacted with aldehyde bearing/free reducing sugars under the heating condition to afford N–O-linked 1,1-/1,5/1,6-disaccharide mimetics in a good yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c03097