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Thiazolylketol Acetates as Glycosyl Donors: Stereoselective Synthesis of a C-Ketoside
Journal article   Open access   Peer reviewed

Thiazolylketol Acetates as Glycosyl Donors: Stereoselective Synthesis of a C-Ketoside

Clark Ferrari, Alessandro Dondoni and Alberto Marra
Molbank, Vol.2024(3)
23/09/2024

Abstract

carbohydrates C-glycosides glycosylation thiazole
We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors in the presence of O-, N-, and P-nucleophiles. We describe here their first use in the C-glycosidation using trimetylsilyl cyanide as the acceptor in order to prepare, after thiazole-to-formyl unmasking and reduction, the corresponding C-ketosides.
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