Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation.
A new method for intramolecular oligosaccharide synthesis that is conceptually related to the general molecular clamp approach is introduced. Exceptional α-selectivity has been achieved in a majority of applications. Unlike other related concepts, this approach is based on the bisphenol A template, which allows one to connect multiple building blocks to perform templated oligosaccharide synthesis with complete stereoselectivity. This principle was demonstrated by the synthesis of an α,α-linked trisaccharide.
Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
Papapida
P
Pornsuriyasak
Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
Xiao G
XG
Jia
Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
Sophon
S
Kaeothip
Department of Chemistry and Biochemistry, University of Missouri-St. Louis , One University Boulevard, St. Louis, Missouri 63121, United States.
Alexei V
AV
Demchenko
D002236:Carbohydrate Conformation; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009844:Oligosaccharides