A novel sugar-based macrocycle consisting of a phosphate-linked 12-membered disaccharide ring (cyclic phosphate-linked oligosaccharide, CyPLOS), fused to two 18-crown-6 ether residues, is here described. The synthesis of the target compound has been accomplished in 23% overall yield for 11 reaction steps, exploiting phosphoramidite chemistry for the dimerization and a classical phosphotriester methodology for the cyclization reaction. NMR-based conformational analysis studies have been carried out on the fully deprotected macrocycle, showing a characteristic arched-structure with C(2)-symmetry.
Synthesis and conformational analysis of a novel carbohydrate-fused bis-crown ether: crown-CyPLOS / C., Coppola; A., Virno; DE NAPOLI, Lorenzo; Randazzo, Antonio; Montesarchio, Daniela. - In: TETRAHEDRON. - ISSN 0040-4020. - ELETTRONICO. - 65:47(2009), pp. 9694-9701. [10.1016/j.tet.2009.09.100]
Synthesis and conformational analysis of a novel carbohydrate-fused bis-crown ether: crown-CyPLOS
DE NAPOLI, LORENZO;RANDAZZO, ANTONIO;MONTESARCHIO, DANIELA
2009
Abstract
A novel sugar-based macrocycle consisting of a phosphate-linked 12-membered disaccharide ring (cyclic phosphate-linked oligosaccharide, CyPLOS), fused to two 18-crown-6 ether residues, is here described. The synthesis of the target compound has been accomplished in 23% overall yield for 11 reaction steps, exploiting phosphoramidite chemistry for the dimerization and a classical phosphotriester methodology for the cyclization reaction. NMR-based conformational analysis studies have been carried out on the fully deprotected macrocycle, showing a characteristic arched-structure with C(2)-symmetry.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
