Photoinduced thiol-ene coupling as a click ligation tool for thiodisaccharide synthesis.
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.
Fiore
Michele
M
Dipartmento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy.
Marra
Alberto
A
Dondoni
Alessandro
A
D000475:Alkenes; D004187:Disaccharides; D055668:Photochemical Processes; D013865:Thioglycosides / Q000138:chemical synthesis*; D054330:Thiosugars / Q000138:chemical synthesis
D000475:Alkenes; D004187:Disaccharides; D013865:Thioglycosides; D054330:Thiosugars