Synthesis and characterization of new aromatic aldehyde/ketone 4-(β-d-glucopyranosyl)thiosemicarbazones

A series of 22 aromatic aldehyde/ketone 4-(β-d-glucopyranosyl)thiosemicarbazones have been synthesized by condensation of 4-(per-O-acetylated-β-d-glucopyranosyl)thiosemicarbazide with an aldehyde or a ketone, and then, deacetylation of the resulting product. The compounds were fully characterized by spectroscopic techniques, elemental analysis, and for two derivatives by X-ray analysis. The data indicate the β configuration, and the E configuration pertaining to the stereochemistry of the Cdouble bond; length as m-dashN bond. However, a partial conversion of the E-form into the Z-form is possible in solution after several hours.