Sulfide-mediated dehydrative glycosylation.
The development of a new method for glycosylation with 1-hydroxy glycosyl donors employing dialkyl sulfonium reagents is described. The process employs the reagent combination of a dialkyl sulfide and triflic anhydride to effect anomeric bond constructions. This controlled dehydrative coupling of various C(1)-hemiacetal glycosyl donors and nucleophilic acceptors proceeds by way of a sulfide-to-sulfoxide oxidation process in which triflic anhydride serves as the oxidant.
Nguyen
H M
HM
Department of Chemistry, Roger Adams Laboratory, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
Chen
Y
Y
Duron
S G
SG
Gin
D Y
DY
D006001:Glycoconjugates / Q000138:chemical synthesis; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D006001:Glycoconjugates; D009844:Oligosaccharides; D013440:Sulfides; D014867:Water; D012451:Safrole; C005746:sulfoxide