35017-25-5Relevant academic research and scientific papers
Influence of the oxime and anomeric configurations on the stability of 2-deoxy-2-hydroxyimino-D-hexopyranosides
Cyman, Magdalena,Wielińska, Justyna,Myszka, Henryk,Trzybiński, Damian,Sikorski, Artur,Nowacki, Andrzej,Liberek, Beata
, p. 558 - 569 (2016)
The Z/E isomerisations of the synthesized benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-D-hexopyranosides during the NMR measurement and during the Zemplén O-deacetylation were observed. In order to study stabilities and tendency of the obtained compounds to isomerise, B3LYP/6-311++G?? level geometry optimisations for four stereoisomers of methyl 2-deoxy-2-hydroxyimino-D-arabino-hexopyranosides in both the O-acetylated and O-deacetylated forms were performed. The results of our theoretical studies are fully in agreement with the experimental data and NMR analysis. Additionally, a single-crystal X-ray diffraction data for benzyl 2-deoxy-2-hydroxyimino-α-D-lyxo-hexopyranoside are reported to supplement our theoretical studies.
