Journal
CHEMICAL SCIENCE
Volume 10, Issue 2, Pages 508-514Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc02788a
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Funding
- Marie-Curie Action COFUND [11/SIRG/B2154]
- Irish Research Council [GOIPG/2013/301]
- Science Foundation Ireland [15/CDA/3625]
- Science Foundation Ireland (SFI) [11/SIRG/B2154, 15/CDA/3625] Funding Source: Science Foundation Ireland (SFI)
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Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%. It is proposed that in these glycosylations thiouracil, monothiophthalimide, and the previously reported catalyst, Schreiner's thiourea, do not operate via a double H-bonding mechanism but rather by BrOnsted acid/base catalysis. In addition to the synthesis of 2-deoxyglycosides and glycoconjugates, we report the first organocatalytic synthesis of 1,1-linked trehalose-type sugars.
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