Efficient installation of beta-mannosides using a dehydrative coupling strategy.
[reaction: see text]. A new coupling procedure for the construction of the challenging beta-mannosidic bond is described. Dehydrative mannosylation using 4,6-O-benzylidene mannopyranoses allows for the formation of beta-mannosides in excellent yield. The stereoselectivity is generally good but influenced by the exact nature of the glycosylating agent and the nucleophile.
Codée
Jeroen D C
JD
Laboratorium für Organische Chemie, ETH Zürich, Switzerland.
Hossain
Laila H
LH
Seeberger
Peter H
PH
D020650:Combinatorial Chemistry Techniques; D008362:Mannosides / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D008362:Mannosides