Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides.
[reaction: see text] Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.
van den Bos
Leendert J
LJ
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Codée
Jeroen D C
JD
van der Toorn
John C
JC
Boltje
Thomas J
TJ
van Boom
Jacques H
JH
Overkleeft
Herman S
HS
van der Marel
Gijsbert A
GA
D003497:Cyclic N-Oxides; D020719:Glucuronides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D010084:Oxidation-Reduction; D013452:Sulfonium Compounds; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis*
D003497:Cyclic N-Oxides; D020719:Glucuronides; D013452:Sulfonium Compounds; D013457:Sulfur Compounds; D013865:Thioglycosides; D014312:Trisaccharides; C003959:TEMPO