Thiouracil-Catalysed Ferrier Rearrangement

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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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Thiouracil-Catalysed Ferrier Rearrangement

Dionysia Pepe 1 , Eoghan McGarrigle 1

1 University College Dublin, Dublin, Ireland

Previously it has been reported from our group that thiouracil catalyses stereoselective glycosylations with galactals in loadings as low as 0.1 mol%. However, glycosylations with glucal and rhamnal gave an inseparable mixture of Ferrier products and desired disaccharide (Scheme 1).[1]

This project focuses on the Ferrier rearrangement which occurs in the reaction of the glycals with the thiouracil catalyst. The reaction has been optimised and benzyl protected glycals, such as glucal, gulal, allal and rhamnal gave the Ferrier product with satisfactory αselectivity. Furthermore, making use of the bulkier tert-butyldimethylsilyl protecting group, the reaction gave two easily separable glycosides, the Ferrier rearrangement product as minor and the desired disaccharide as major. To our delight, introducing the tert-butyloxycarbonyl protecting group, the glycosylation reaction with sugar, non-sugar and amino-acid acceptors led to the desired products after an intermolecular Ferrier rearrangement (Scheme 2).

G. A. Bradshaw, A. C. Colgan, N. P. Allen, I. Pongener, M. B. Boland, Y. Ortin, E. M. McGarrigle, Chem. Sci., 2019,10, 508-514

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European Carbohydrate Organisation

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