Photoinduced thiol-ene coupling as a click ligation tool for thiodisaccharide synthesis

Abstract

(Chemical Equation Presented) The high efficiency and selectivity of the thiol-ene radical reaction has been validated by the photoinduced coupling of anomeric sugar thiols with sugar alkenes to give 1,6-linked S-disaccharides in good to excellent yields (76-92%) and high diastereoselectivities (up to 99%). The reaction appears to be well-qualified as an exemplar click process. © 2009 American Chemical Society.