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Synthesis and conformational analysis of a novel carbohydrate-fused bis-crown ether: crown-CyPLOS
Authors:Cinzia Coppola  Lorenzo De Napoli  Daniela Montesarchio
Institution:a Dipartimento di Chimica Organica e Biochimica, Università di Napoli ‘Federico II’, Via Cintia, 4, I-80126 Napoli, Italy
b Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli ‘Federico II’, Via D. Montesano 48, I-80131 Napoli, Italy
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 C2-symmetry.
Keywords:Chemical synthesis  Macrocycles  Carbohydrates  Crown ether derivatives  NMR
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