Synthesis and conformational analysis of a novel carbohydrate-fused bis-crown ether: crown-CyPLOS |
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Authors: | Cinzia Coppola Lorenzo De Napoli Daniela Montesarchio |
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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 |
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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. |
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Keywords: | Chemical synthesis Macrocycles Carbohydrates Crown ether derivatives NMR |
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