Synthesis of Spirocyclic Cyclopropyl Glycosyl-1-phosphate Analogues
1Department of Chemistry, Laboratory of Bio-Organic Chemistry - NAmur Research Institute for LIfe Sciences (NARILIS), University of Namur (UNamur), 5000 Namur, Belgium.
Abstract:
A general methodology allowing the preparation of phosphonylated 1-spirocyclopropyl analogues of glycosyl-1-phosphates is reported. The scope of this reaction has been assessed using various exo-glycals easily obtained from the corresponding pyranoses and furanoses. The cyclopropanation was found to be stereospecific, and the cis/trans selectivity only depends on the E/Z configuration of the starting exo-glycal. The four possible isomers of spirocyclopropyl ribose-1-phosphonate could thus be prepared in a controlled manner, protected and deprotected.
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