AMMONOLYSIS OF PENTA-O-BENZOYL-α-D-GLUCOPYRANOSE IN AN APROTIC MEDIUM. CHARACTERIZATION OF THE PRODUCTS ISOLATED, AND CONFORMATIONAL ANALYSIS OF ELEVEN N-BENZOYL-D-GLUCOFURANOSYLAMINE DERIVATIVES

Article abstract of DOI:10.1016/0008-6215(87)85006-1

The reaction of penta-O-benzoyl-α-D-glucopyranose with chloroform-1,4-dioxane-liquid ammonia gave 1,1-bis(benzamido)-6-O-benzoyl-1-deoxy-D-glucitol (29.0percent), three partially benzoylated derivatives of N-benzoyl-α-D-glucofuranosylamine (23.6percent), a small proportion of N-benzoyl-di-O-benzoyl-β-D-glucofuranosylamine (0.2percent), and four partially benzoylated derivatives of α-D-glucopyranose (9.9percent).The structures of the hitherto-unknown products, and their anomeric configurations, were established by chemical and spectroscopic methods.The conformations in solution of both anomers of N-benzoyl-D-glucofuranosylamine, their partially benzoylated derivatives isolated from the ammonolysis reaction, and the per-O-acetyl derivatives of the various compounds were analyzed by (1)H-n.m.r.spectroscopy.