Development of a synthetic method for the preparation of L-hexoses for
synthesis of oligosaccharides and their applications for the economical
synthesis of heparin analogues
The rare, but biologically widespread L-hexoses and their corresponding 6-deoxy counterparts play important roles in nature1. Although L-hexoses are not as prevalent as their enantiomers, the D-hexoses, numerous significant biomolecules contain L-sugars. The Lsugars are commercially available but most of them are very expensive (Table 1.). Therefore, it is important to produce L-sugars from common carbohydrates, which has always been a major challenge for chemists in the history of carbohydrate chemistry....(more)
Investigator: Dr. Mihály Herceg
Work plan
First year
- Preparation of the α-ethylthio-glucopyranoside in large scale, introduction of the proposed protecting groups (ester, ether), synthesis of 5,6-unsaturated d-glucose derivatives, optimization of the elimination reaction
- Synthesis of the D-allose from D-glucose in large scale, preparation of the α-ethylthio-alloside and formation of the intended protecting groups, synthesis of 5,6-unsaturated D-allose derivatives
- Perform of the hydroboration/oxidation test reactions, optimization; characterization of the obtained L-sugars
- Testing of the 4,6-acetal ring closure reactions and transformation of the L-sugar into donors
- Further transformation of the L-ido and L-talo configured derivatives
- Publication of the results in referred international journal (2 publication)
Second year
- Preparation of the L-altro and L-manno derivatives, characterization of the obtained L-sugars
- Synthesis of the α-ethylthio-mannopyranoside in large scale, introduction of the proposed protecting groups (ester, ether), synthesis of 5,6-unsaturated D-glucose derivatives, optimization of the elimination reaction
- Synthesis of the L-idose donor in large scale for the preparation of Fondaparinux
- Preparation of D-aldose derivative in large scale from the planned D-mannose derivative
- Synthesis and transformation of the L-gulose and L-galactose derivatives
- Publication of the results in referred international journal (3 publications)
- Publication of the results in a PhD dissertation
Third year
- Synthesis of the 5,6-unsaturated D-altrose derivatives, optimization of the elimination reaction on the given derivatives
- Preparation of the glucosamine monomers in large scale for the synthesis of Fondaparinux
- Preparation of the L-allose and L-glucose derivatives, configuration analysis
- Synthesis of glucuronic acid precursor for the production of Fondaparinux
- Optimization of the glycosylation reactions, synthesis of the DE disaccharide donor and the FGH trisaccharide acceptor
- Preparation of the protected pentasaccharide by [2+3] block synthesis, formation of the final groups, structural analysis
- Publication of the results in referred international journal (3 publications)