Development of an efficient, regio- and stereoselective route to libraries based on the beta-D-glucose scaffold.
The design and execution of an efficient synthetic route for the sequential functionalization of the five hydroxyl substituents of beta-D-glucose has been achieved. This strategy, based on the stereoselective glycosidation of thioglycosides, provides a new approach for the parallel construction of a wide variety of beta-D-glucose analogues and as such holds promise for solid-support library syntheses.
Hirschmann
R
R
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Ducry
L
L
Smith
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AB
D002219:Carbamates / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D002219:Carbamates; D006027:Glycosides; D005947:Glucose