Synthesis and Structural Characterization of Haloaryl N‐Substituted Sugar Derivatives

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.