Oxidation of aldose oximes. Formation and structure of hydroxydiazene oxide acetals and preparation of hydroximolactones. X-Ray crystal structure of 2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl-ONN-azoxy 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside

摘要: Oxidation of the glucopyranosylamine (1) with peracid gave, in low yield, either stable 1-deoxy-1-nitrocompound (2) or dimer (3), depending on reaction conditions. oximes (4), (9), (13), and (17) periodate at pH gave hydroxiolactones (5), (10), (14), (18), respectively, and, case oxime (17), (20) also [at higher pH]. The structure compound was determined by X-ray analysis. structures hydroximolactones were deduced from spectroscopic data chemical transformations; they obtained high yield aforementioned oxidation pH.