Thesis topic proposal
Marietta Vágvölgyiné dr. Tóth
Synthesis and transformations of sugar imine type derivatives


Institute: University of Debrecen
Doctoral School of Chemistry

Thesis supervisor: Marietta Vágvölgyiné dr. Tóth
Location of studies (in Hungarian): Debreceni Egyetem TTK Szerves Kémiai Tanszék E/421 kutató laboratórium
Abbreviation of location of studies: E421

Description of the research topic:

Sugar imine type derivatives (anhydro-aldose and aldono-lactone tosylhydrazones, anhydro-aldoximes, etc.) are valuable building blocks of synthetic carbohydrate chemistry. Their chemical transformations to be investigated are a hardly ever studied field of carbohydrate chemistry. In the last decade several papers were published focusing on the application of N-tosylhydrazones in coupling reactions. A systematic study on the applicability of sugar tosylhydrazones in coupling reactions has been started in our research group resulting in the formation of C-O, C-S, C-C and C-N bonds using anhydro-aldose tosylhydrazones as coupling agents. In this project we plan to extend these methods for aldono-lactone tosylhydrazones. Based on the chemistry worked out in our group for the synthesis of anhydro-aldoximes with one example for an anhydro-aldoxime ether the synthesis of further aryl ether derivatives and oximes with two sugar units are planned. Alternative reaction pathways to get these anhydro-aldoxime ethers can be the O-arylation/glycosylation of aldoximes using catalytic methods and the acid catalyzed addition of aldoximes to unsaturated sugar derivatives (endo- and exo-glycals). After removal of the protecting groups, D-galacto configured molecules will be tested as galectin inhibitors.

Required language skills: English
Further requirements: 
Skills in preparative organic chemistry as well as in NMR spectroscopy

Number of students who can be accepted: 1

Deadline for application: 2023-05-15

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