Synthesis and Structural Characterization of Haloaryl N‐Substituted Sugar Derivatives

• Published in: European journal of organic chemistry 2024-10, Vol.27 (46), p.n/a
• Main Authors: Rengel, Natividad Bejarano, Esteche, Juliana, Echeverría, Gustavo A., Piro, Oscar E., Santiago, Cintia C., Ponzinibbio, Agustín
• Format: Article
• Language: English
• Subjects: 6-amino-6-deoxy-galactosides; Galactosides; Haloaryl carbohydrates; NMR; Nuclear magnetic resonance; Structural analysis; Structural X-ray diffraction
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202400802

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. We report the synthesis 6‐N‐haloaryl‐galactosides, a family of 6‐deoxy‐1,2;3,4‐di‐O‐isopropylidene‐6‐N‐phenylamino‐α‐D‐galactopyranosides were prepared and structurally analyzed by X‐ray diffraction techniques and NMR spectroscopy, we also included the study of an unexpected N,N'‐diphenylamino by‐product; relevant conformational aspects in solution and in the solid state are identified and discussed.