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Synthesis and Structural Characterization of Haloaryl N‐substituted Sugar Derivatives

2024; Wiley; Linguagem: Inglês

10.1002/ejoc.202400802

1434-193X

Natividad Bejarano Rengel, Juliana Esteche, Gustavo A. Echeverría, Oscar E. Piro, Cintia C. Santiago, Agustı́n Ponzinibbio,

Glycosylation and Glycoproteins Research

We present here the efficient preparation of 6‐N‐haloaryl‐galactosides through a reductive amination process. A complete set of 6‐deoxy‐1,2;3,4‐di‐O‐isopropylidene‐6‐N‐phenylamino‐α‐D‐galactopyranosides were obtained with a straightforward method. The products were structurally analyzed by X‐ray diffraction techniques and NMR spectroscopic data. A complete investigation of the galactosyl derivatives is described, including an unexpected N,N´‐diphenylamino by‐product. Moreover, relevant conformational aspects in solution and in the solid state are identified and discussed.