Radical-mediated synthesis of alpha-C-glycosides based on N-acyl galactosamine.
[structure] C-Glycosides of N-acyl 2-amino-2-deoxygalactose (acyl = MeCO, CF(3)CO, t-BuOCO) are available in a stereoselective manner by trapping of an anomeric radical with an activated alkene. Using anomeric selenides, radical generation and trapping is carried out under conditions that avoid competitive reduction, and this chemistry has been applied to the synthesis of the novel C-glycoside analogue of O-benzyl alpha-D-GalNAc.
SanMartin
R
R
School of Chemistry, University of Bristol, Bristol BS8 1TS, UK.
Tavassoli
B
B
Walsh
K E
KE
Walter
D S
DS
Gallagher
T
T
D000475:Alkenes / Q000737:chemistry; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D005609:Free Radicals / Q000737:chemistry; D005688:Galactosamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis*
D000475:Alkenes; D001593:Benzyl Compounds; D005609:Free Radicals; D006027:Glycosides; D005688:Galactosamine