Two tetravalent lactosidic scaffolds have been synthesised in solution from commercial lactose. Careful manipulation of the protecting groups allowed us to orthogonally protect four OH groups for their use as diversity sites for the development of broad screening libraries of sugar mimics. The selective access to each of these hydroxy groups has been demonstrated on scaffold 2 by deprotection and functionalisation with p-fluorophenyl isocyanate. Finally, the 6-OH derivative of compound 2 was covalently attached to a polymeric support.
Solution Synthesis of Two Orthogonally Protected Lactosides as Tetravalent Disaccharide-Based Scaffolds / S. Castoldi, M. Cravini, F. Micheli, E. Piga, G. Russo, P. Seneci, L. Lay. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2004:13(2004), pp. 2853-2862. [10.1002/ejoc.200300807]
Solution Synthesis of Two Orthogonally Protected Lactosides as Tetravalent Disaccharide-Based Scaffolds
G. Russo;P. SeneciPenultimo
;L. LayUltimo
2004
Abstract
Two tetravalent lactosidic scaffolds have been synthesised in solution from commercial lactose. Careful manipulation of the protecting groups allowed us to orthogonally protect four OH groups for their use as diversity sites for the development of broad screening libraries of sugar mimics. The selective access to each of these hydroxy groups has been demonstrated on scaffold 2 by deprotection and functionalisation with p-fluorophenyl isocyanate. Finally, the 6-OH derivative of compound 2 was covalently attached to a polymeric support.
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