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Vorträge und Posterpräsentationen (ohne Tagungsband-Eintrag):

C. Stanetty, M. Draskovits, M.D. Mihovilovic:
"The Acyloxyallylation of Aldoses - Understanding and Applications";
Vortrag: 17. Österreichische Chemietage 2017, Salzburg (eingeladen); 25.09.2017 - 28.09.2017.



Kurzfassung englisch:
The lack of easy availability of even simple monosaccharides and, consequently, the restriction of methodology limited only to readily obtainable prototype carbohydrates is an accepted burden in carbohydrate chemistry to date. We see the need to improve on such shortcomings at high priority to bring the important field of carbohydrate chemistry more to the center of attention and application. The indium-mediated acyloxyallylation of aldoses is an elegant way for the two-carbon homologation of reducing sugars (upon ozonolysis), however it remained understudied and underused. We have recently developed the original prove-of-concept study into the first short, large-scale synthesis of the important bacterial sugar L-glycero-D-manno heptose. En route, we have identified and quantified all diastereomers formed, now allowing predictions on the type of selectivity observed. Subsequently, we studied protected and unprotected tetroses as starting materials and could reveal a consistent pattern in the product distribution for two alternative relative stereo-chemical configurations as found in erythrose and threose. Furthermore, diasterodivergence was observed between corresponding pairs of 2O,3O protected and unprotected starting materials. The latter finding lead to short scalable routes to L allose and L-talose, two further rare sugars made readily available by the means of acyloxyallylation.


Elektronische Version der Publikation:
https://publik.tuwien.ac.at/files/publik_264393.pdf


Erstellt aus der Publikationsdatenbank der Technischen Universität Wien.