Galacto, gluco, manno, and disaccharide-based C-glycosides of 2-amino-2-deoxy sugars.
[reaction: see text] Starting from readily available precursors, selenoglycosides derived from GalNAc, GlcNAc, and ManNAc were prepared by either a one- or a two-step process. The anomeric selenides underwent facile C-Se homolysis to provide the corresponding anomeric radicals, which were trapped with alkenes to give C-glycosides. This provides a general entry to alpha-C-glycosides based on 2-amino-2-deoxy sugars that is also applicable to disaccharide variants.
Grant
Laura
L
School of Chemistry, University of Bristol, Bristol BS8 1TS, UK.
Liu
Yan
Y
Walsh
Kenneth E
KE
Walter
Daryl S
DS
Gallagher
Timothy
T
D000606:Amino Sugars / Q000138:chemical synthesis*; D004187:Disaccharides / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006027:Glycosides; D008358:Mannose / Q000737:chemistry; D009005:Monosaccharides / Q000138:chemical synthesis*; D018036:Selenium Compounds
D000606:Amino Sugars; C438934:C-glycoside; D004187:Disaccharides; D006027:Glycosides; D009005:Monosaccharides; D018036:Selenium Compounds; D005947:Glucose; D008358:Mannose; D005690:Galactose