Journal
TETRAHEDRON
Volume 65, Issue 47, Pages 9694-9701Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.09.100
Keywords
Chemical synthesis; Macrocycles; Carbohydrates; Crown ether derivatives; NMR
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Funding
- MIUR (PRIN)
- Centro di Metodologie Chimico-Fisiche (CIMCF)
- Universita di Napoli 'Federico II'
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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. (C) 2009 Elsevier Ltd. All rights reserved.
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