Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors.
[reaction: see text] A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph(2)SO/Tf(2)O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator system to furnish trisaccharides. The alpha-Gal epitope and a hyaluronan trisaccharide were efficiently assembled in a one-pot procedure.
Codée
Jeroen D C
JD
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
van den Bos
Leendert J
LJ
Litjens
Remy E J N
RE
Overkleeft
Herman S
HS
van Boom
Jacques H
JH
van der Marel
Gijs A
GA
D002240:Carbohydrate Sequence; D006031:Glycosylation; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D014312:Trisaccharides / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D014312:Trisaccharides