Synthesis of Spirocyclic Cyclopropyl Glycosyl-1-phosphate Analogues

A general methodology allowing the preparation of phosphonylated 1-spirocyclopropyl analogues of glycosyl-1phosphates 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.

Automated summary

A general methodology for preparing phosphonylated 1-spirocyclopropyl analogues of glycosyl-1phosphates is reported. The reaction showed stereospecificity, with cis/trans selectivity depending on the E/Z configuration of the starting exo-glycal. Four different spirocyclopropyl ribose-1-phosphonate isomers could be prepared in a controlled manner.