Left to right: Mc Carthy, Zhu
Cian Mc Carthy obtained his B.Sc. degree in Medicinal Chemistry from University College Dublin. He is currently a final year PhD student under the guidance of Xiangming Zhu, investigating the role of N-trifluoromethylthiosaccharin as a promoter for thioglycoside activation.
Xiangming Zhu was born in Yiwu City, China. He received his PhD from Shanghai Institute of Organic Chemistry in 2001. He then moved to Konstanz to take up a postdoctoral position at the University of Konstanz with Prof Richard Schmidt. In 2005, he joined Prof. Geert-Jan Boons’ group in the Complex Carbohydrate Research Centre at UGA to work on the stereoselective synthesis of arabinofuranosides. He is currently a PI in the School of Chemistry at UCD and his research interests are in the areas of carbohydrate chemistry.
What inspired your research in this area?
A direct and highly stereoselective procedure for the synthesis of α-glycosyl thiols (J. Org. Chem. 2011, 76, 10187-10197) has been developed recently in our laboratory. α-Glycosyl thiols could be used to make various α-S-linked glycosides or glycoconjugates including α-thioglycoside donors, are thus very valuable building blocks in thioglycoside chemistry. This work was therefore initiated as part of our research program aimed to investigate glycosylation property of α-thioglycoside donors.
What do you personally feel is the most important outcome of your study?
I believe the most significant finding of this study is the simplicity of the reaction condition that achieves high chemoselectivity between two most commonly used thioglycoside donors. Our study highlights the importance of finding new activation protocols which may bring new and interesting applications to glycosylation.
What directions are you planning to take with your research in future?
We would like to expand our study beyond phenyl and ethyl thioglycosides to the commonly used S-tolyl glycoside donors. This will give an even more comprehensive overview of our new promoter’s ability in chemoselective activation. Additionally, we would like to see how effective N-trifluoromethylthiosaccharin will serve as an extension to already established reactivity-based one-pot strategies.
Read the full article: Chemoselective Activation of Ethyl vs Phenyl Thioglycosides: One-pot Synthesis of Oligosaccharides
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