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...
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2022-04, Vol.87 (8), p.5125-5135 |
---|---|
Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
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 |