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Radical-mediated synthesis of alpha-C-glycosides based on N-acyl galactosamine
R SanMartin1, B Tavassoli, K E Walsh
1School of Chemistry, University of Bristol, Bristol BS8 1TS, UK.
Organic Letters
|December 12, 2000
Abstract:
[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.