Sensible improvements induced by ionic liquids in the reaction of modified carbasugars with bases for the building of constrained carbanucleosides.
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.
Paoli
M Laura
ML
Dipartimento Farmaco-Chimico-Tecnologico, Università degli Studi di Siena, Via A. Moro, 53100 Siena, Italy.
Piccini
Sonia
S
Rodriquez
Manuela
M
Sega
Alessandro
A
D002241:Carbohydrates / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry
D002241:Carbohydrates; D007477:Ions; D009705:Nucleosides; D012997:Solvents