Efforts to Effect Regio- and Stereoselective Glycosylations

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Programme Social programme Plenary speakers Keynote speakers 1st EuroCarb Young Researcher (ECYR) Workshop CarboMet Workshop Mini symposium: Glycobiology at the LUMC and beyond Favourites/Agenda

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1st EuroCarb Young Researcher (ECYR) Workshop

CarboMet Workshop

Mini symposium: Glycobiology at the LUMC and beyond

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Efforts to Effect Regio- and Stereoselective Glycosylations

Eoghan McGarrigle 1 , Roisin McCarthy 1 , Dionissia Pepe 1 , Avene Colgan 1 , Ande Chennaiah 1

1 University College Dublin, Dublin, Ireland

Previously[1-4], we have reported on organocatalysed glycosylations using glycal donors and acceptors containing single unprotected hydroxy groups. This presentation will detail our efforts to effect regioselective and stereoselective glycosylations using organocatalysts and the differences observed when using diols as substrates compared to mono-ols. Galactose acceptors were chosen in order to systematically probe the regioselectivity of reactions with glycals.

Secondly, we will describe our efforts to use and combine Demchenko's concept of H-Bond-mediated Aglycone Delivery for stereoselective glycosylation[5], with Taylor's system for boron-mediated regioselective glycosylations[6] to effect stereo- and regioselective glycosylations. Some of these ideas have also been used in our efforts to design switchable 'bi-modal' donors[7,8], the results of which will be presented.

E. I. Balmond, D. M. Coe, M. C. Galan, E. M. McGarrigle, Angew. Chem. Int. Ed. 2012, 51, 9152.

A. C. Colgan, H. Müller-Bunz, E. M. McGarrigle, J. Org. Chem. 2016, 81, 11394.

G. A. Bradshaw, A. C. Colgan, N. P. Allen, I. Pongener, M. B. Boland, Y. Ortin, E. M. McGarrigle, Chem. Sci. 2019, 10, 508.

S. Medina, M. Harper, E. I. Balmond, S. Miranda, G. Crisenza, D. M. Coe, E. M. McGarrigle, M. C. Galan, Org. Lett. 2016, 18, 4222.

J. P. Yasomanee, A. V. Demchenko, J. Am. Chem. Soc. 2012, 134, 20097.

C. Gouliaras, D. Lee, L. Chan, M. S. Taylor, J. Am. Chem. Soc. 2011, 133, 13926.

A. K. Kayastha, X. G. Jia, J. P. Yasomanee, A. V. Demchenko, Org. Lett. 2015, 17, 4448.

F. Ding, A. Ishiwata, Y. Ito, Org. Lett. 2018, 20, 4384.

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