A series of 22 aromatic aldehyde/ketone 4-(beta-D-glucopyranosyl)thiosemicarbazones have been synthesized by condensation of 4-(per-O-acetylated-beta-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 beta configuration, and the E configuration pertaining to the stereochemistry of the C=N bond. However, a partial conversion of the E-form into the Z-form is possible in solution after several hours.

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http://dx.doi.org/10.1016/j.carres.2009.05.010DOI Listing

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