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301. Sensible Improvements Induced by Ionic Liquids in the Reaction of Modified Carbasugars with Bases for the Building of Constrained Carbanucleosides

Author

Sonia Piccini, Manuela Rodriquez, Alessandro Sega, and M. Laura Paoli

Subjects
Ions, Bicyclic molecule, Molecular Structure, Organic Chemistry, Carbohydrates, Carbasugars, Nucleosides, Chemical synthesis, chemistry.chemical_compound, Enantiopure drug, chemistry, Ionic liquid, Solvents, Organic chemistry
Abstract

Starting from racemic 4-hydroxy-4-methyl-2-cyclopentenone, a family of enantiopure carbanucleosides locked in the northern conformation has been synthesized. The use of ionic liquids was determinant in the last step resulting in a tangible increase of the yields and dramatic reduction of reaction times and volumes of organic solvents. To our knowledge, this is the first example of the use of ionic liquids in the coupling of carbasugars with heterocyclic bases.

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