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Vorträge und Posterpräsentationen (mit Tagungsband-Eintrag):

C. Stanetty, M. Draskovits, H. Kalaus, A. Reichetseder, M.D. Mihovilovic:
"Sugars: Sweet Tales From an Aldehyde's Perspective";
Vortrag: XXth European Carbohydrate Symposium (EUROCARB2019), Leiden; 30.06.2019 - 04.07.2019; in: "EuroCarb2019 Abstract Book", (2019), 203 S.



Kurzfassung englisch:
Our research focuses on the development of new synthetic methodology for the interconversion of abundant sugars
to more exotic ones utilizing the natural reactivity of the aldehyde moiety. The open chain content generally
represents a minute minority in reducing sugars´ equilibria (dominated by the hemiacetal forms), which is usually too
small to be determined efficiently and/or accurately. To overcome this issue, we have developed an assay based on
the adduct formation of a strongly UV-active aminal species which thereby translates the open chain proportion into
a readily measurable reaction rate (see Figure 1, middle). [1] We have confirmed the validity of the approach
measuring all parent hexoses and pentoses and exhibiting a high degree of consistency with literature data.
Next, we went on to apply the assay to real cases from the field of indium mediated acyloxyallylation [2] (Figure 1,
bottom) and our current study of the organocatalytic anomeric activation by N-heterocyclic carbenes (NHCs) which
we are developing into a controlled dehomologation methodology (Figure 1, top). [3] In both areas we have
encountered unexpected reaction outcomes which could not be explained by the sole chemical vicinity of the
aldehyde function but could be correlated to the differences in the ratios of available open chain content within
relevant starting materials, intermediates and products.

[1] Reichetseder, A; Kalaus, H. Stanetty, C.;* Mihovilovic, M. D; in preparation
[2] Draskovits, M.; Stanetty, C.;* Baxendale, I. R.; Mihovilovic, M. D; J. Org. Chem. 2018, 83 (5), 2647-2659.
[3] Draskovits, M.; Kalaus, H. Stanetty, C.;* Mihovilovic, M. D; submitted 2019


Elektronische Version der Publikation:
https://publik.tuwien.ac.at/files/publik_284219.pdf



Zugeordnete Projekte:
Projektleitung Christian Stanetty:
Kontrollierter Zuckerabbau durch N-Heterocyclische Carbene


Erstellt aus der Publikationsdatenbank der Technischen Universität Wien.